But I learned that the work really doesn't care who does it, as long as it gets done, and eventually I became a rather good handyman and parlayed that into DIY landlording as a way to break into the market here.If you're determined to stay in Boston, I cannot recommend getting out to local real estate associations and talking to other local investors highly enough.

Lock in your money now and as rates continue to rise you'll see more and more rentors staying in the rental market longer.But beware because the rising interest rate climate could change quickly and with a correction we could see govt policy in a heartbeat that reduces barriers to borrowing and ownership. 

They can STAY and get their other deposit money back, there is no gun to their head. 

If he’s “financing” the purchase that means you’re buying sub2 or on a wrap, the loan stays in his name so he probably won’t qualify for another loan.

I rent to people that normally would stay in a motel for a month or two. 

Those who remain interested and are willing to fight for your business or at minimum stay engaged, are the type of people you want to work with.In terms choosing an agent, explain to the others that you've connected with someone else who you feel is able to help with your needs (if they even follow up). 

@Cassandra Staffieri this is the latest news on the Nola STR climate. https://www.google.com/amp/s/www.theadvocate.com/gambit/new_orleans/news/article_9cbb3e40-c75e-11e8-82fc-dfda324cdedd.amp.htmlI would be patient and stay tuned if I were you.

The other investor would like to stay off any type of loan. 

Still would stay owner occupied....Thus removing the PMI and giving the experience qualifications?

If you do run across those, stay away!