I first want to learn the business and seek possible mentorship before tackling the market. 

Good luck with the project, that's great that you can tackle that type of stuff!

I've been a lender for more than 30 years and I am still learning every day, but I didn't tackle the cash flow spreads on an office building my first month on the job.

Even if the cash-on-cash return is lower for my first deal, I feel like it would be a nice confidence boost since I still have to tackle other tasks like properly setting up my business entity and dealing with taxes. 

Starting capital will be limited, but I can scale back the first project if needed, which would make borrowing for any of the 3 within reach to tackle first.Any recommendations?

I would not tackle something like this as a beginner without a lot of help. 

Exploring out-of-state flip deals could offer more opportunities, but be prepared for the challenges of remote management and market differences - or the additional costs of property management.To tackle analysis paralysis, consider setting a decision deadline.

Just broaching it in friendly conversation can be a very innocuous form of solicitation. 

@Scott JacobsI don't know the Boston market, but I'll tackle a few of these.

The prices of these cites vary significantly so before I rack up my tab on subscriptions, I wanted to see if anyone in the BP community had any suggestions/advice on how they would tackle finding deals while living in another state.Thanks in advance!