Goal: Lateral to REIB from Valuations

So, I'll give my opinion to your questions. Just note, I am now over a decade from any personal direct attempts at trying to get hired by anything like REIB, so as to current trends and hiring practices that may have shifted, take notes from those more recent!

To your questions..

1. I am not sure a broker position will make you many more appealing to REIB (I severely doubt it for anything like the BB firms), since REIB is just the fancier "sellside", not sure they will look any more favorably to those out of a CBRE/JLL type place, honestly many be a downgrade from what you are doing (that is my honest suspicion) since it is likely "lower tier" analytical work. I also can't think of anyone I know personally doing this jump (unless it was via grad school as impetus), but it may occur, but generally it flows opposite REIB --> brokerage (top tier firms will recruit from BB IB for sure). 

2. To be honest, not sure if "realistic" or not... but I really doubt "impossible". Valuation skills are key to large scale transactions (like M&A), and getting direct hired to a real estate desk seems possible if you can convince the MD that your skills are unique/additive. This is one of those situations where going in higher (like as associate or sr. analyst) may be easier than trying to get entry level analyst, but need to network have some direct connections to make your pitch. The issue is that IB in general (and thus the real estate desks as a result), tend to hire direct from college then promote up, to my knowledge they don't do tons of "experienced" hiring (besides laterals from competitors as needed). It can happen, but the MD/desk really needs to drive it. You could apply to the general entry level pool, but that is really difficult for everyone regardless, but no harm in trying if you would take such a role (I assume they mostly hire from SA programs, but maybe still have open applications, especially if a real estate desk wants someone with legit re knowledge/background, in that case you would fit). As above poster said, probably easier at lower-tier and boutique banks than BB.

3. REIB transactions are heavily reliant on valuation models and valuation exercises, so the more you can assert/prove you "know" how to do the job the better. I really think you are better off "aiming high" for more experienced role where they need/want your background than fighting for open entry level where they frankly don't care (just want the smartest hardest working people willing to work 120 hrs a week and not complain..... experienced hires are not the best fit for this lol). 

Final note.... are you really fixated on REIB for a long-term career? Or are you seeing this as part of some "path" to something else. I only ask because you reference the brokerage role as a "step", that may be just as fulfilling (and even well paid) career than working for a bank. Plus, all the big brokerages have somewhat legit REIB platforms internally that you could attempt to join (not sure they should be at all classed with the big BB type platforms, but they do compete/are legit in many respects). Personally, I'd think a better career in those shops (if on legit, top tier desk) than in general I-banking (which seems shitty IMHO). You may feel different, its totally personal I'd say!