When to buy first investment property?

In my opinion, generally, the best time to buy is now because prices will continue to go up. Yes I know this is the mentality that basically caused 08', but there are major differences between now and then namely 1.) Banks are waaaay more conservative today than they were 20 years ago and even 3 years ago 2.) Interest rates are at a ~15 year high, so it's unlikely you are overpaying for anything since any and all RE bubbles have already burst 3.) The housing crisis has only been getting worse every year esp in Tier 1 markets.

Now that is my general opinion; my more specific opinion for you is to wait and save more because $100k isn't much in the real estate business. I also advise that you purchase in your Tier 1 market instead of a Tier 2 or 3. The reason I advise that you purchase in a Tier 1 market is because demand far outweighs supply compared to Tier 2 and Tier 3 markets. Tier 1 markets are comprised of highly educated, high income earners, but also have the most restrictive zoning laws that constrain supply. As a result, prices can increase significantly year over year. Now I know the counterargument to this typically is that Tier 2/3 markets have more growth potential, but anecdotally I call bullshit on this argument. From personal experience, I think that the delta between supply and demand in Tier 1 cities is so wide (and gets wider every year) that price increase in certain pockets of Tier 1 cities can significantly outpace Tier 1/2 markets. I live and develop real estate in a Tier 1 market and I've never heard of my market or other Tier 1 markets be described as "overbuilt" or "too much supply coming online." We are always described as "housing crisis." Conversely, in Tier 2/3 growth markets such as Texas, Arizona, Nevada, Florida, etc...every couple years you will hear how these markets have been "overbuilt" or there is too much supply and that is because they have much more relaxed zoning laws compared to Tier 1 markets. Anecdotally, I bought my own SFH ~9months ago for $1.2mm and I put in ~$20k to combine 2 small bedrooms to make 1 master bedroom with a master bath and closet i.e. I didn't do much. In the past couple months there have been several comps that have sold between $1.45mm-$1.65mm. I'm actually going to list my property this spring for sale for ~$1.6mm. I'm quite confident I will sell $1.5mm+ and my goal is to rinse and repeat but probably a deeper renovation. So anyways, this is why I think you should buy in a Tier 1 market. Tier 1 is also safer when shit hits the fan and you are within driving distance.

Now before I advise you on what to buy, let's first talk numbers. 3 years ago the primary hurdle to buying a property was having the down payment to do so because rates were so low that if you bought a property, your mortgage was the same or maybe even less than your rent. Today is very different. I would argue that having the income to support a mortgage (assuming only 20%-25% down) is a bigger hurdle than having the down payment. If you buy a $1mm property and put down 20% ($800k mortgage) you're looking at a ~$5k mortgage, after tax, insurance, utilities, it'll be over $6k. That's a lot for 1 person. General rule of thumb is that you make 3x your mortgage payment, so $15k/month or $180k/year and in a Tier 1 market, $1mm really isn't that much. If you use first time home buyer programs where you only need to put down 3%-10%, your monthly payments are even higher.

So given where rates are today, what do I advise? House hack. Buy a 3-4 bedroom SFH and rent out the other bedrooms or buyer a duplex/triplex and rent out the other units. I don't really advise buying condos because they don't appreciate that much (at least that's what I've noticed) and you are competing against the other condos in your building.

When should you buy? Ultimately comes down to money. You need 20%-25% down payment (let's say $1.25mm purchase price) + closing costs (I estimate this ~$10k-$12k) + $50k to renovate if the property is not move in condition (if it is livable, you can renovate as you live in it) +  potential cost of carry while you renovate or find roommates (let's say 3months @ $7k/month depending if renovation is needed or no so ~$20k) + rainy day fund if you need to repair anything or get laid off (let's say 6months of your portion of the rent @ $2k/month, so $12k. You also get 6months of unemployment which gives you roughly a year to find a job). So you're looking at ~$270k-$350k depending on renovation and purchase price. I know this sounds like a lot from where you are now and it is, but you are young and have plenty of time. The first one is the most difficult. Once you've bought the first one and hopefully make a decent profit (hopefully $250-300k+) after 1-2 years, you have a lot more capital for the next one. Alternatively, you could partner up with 1 or 2 friends.

Lastly, and I cannot stress this enough, know your market, know your market, know your market. You must be 110% confident in every property you buy. Investing is all about conviction. While you are saving up, research different markets, go to open houses, ask real estate agents where the hottest markets are. Also, another rule - location, location, location. This is a very nuanced rule because you also have to take into account price, but don't just sacrifice location for a low price. There's a reason the better located property is priced higher. Sometimes it's worth it to pay the premium, but this all comes back to market research and how well you know your market.