Several have mentioned utilizing low down payment second home loans for qualifying.

Go wtih what works - but intelligently.We offer a free month of rent, but to avoid desperate people, we credit 50% towards their 2nd month (to make sure they can afford 1st month rent + SD) and then credit the other 50% the 5th month.

Those are spray and pray techniques that don't fit with sellers right now because sellers/owners are sitting on a very low rate and don't want to move to go up 4-5 points on their rate.Listings aren't a start now thing as well.

I've been self-employed for only 6 months, and loans are proving difficult to come by despite my great credit (not to brag, I'm moreso frustrated and seeking help).

Most non-FHA loans will require at least 15% down but you'll have to have amazing credit.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

Common sources of such properties include:Foreclosures: Homes that have been repossessed by banks due to non-payment.Distressed Properties: Homes that are in poor condition and need a lot of work.Auctions: Properties sold at auction for below market value.Off-market Deals: Properties that aren't listed on the MLS but are available for sale through direct outreach or networking.The key is to buy a property at a price low enough to ensure that even after renovations, the home will appraise for a higher value.2.

I do my own property management to keep my expenses low. 

@Samuel Kim Your wife can meet the 750-hour test for Real Estate Professional Status (REPS) by actively managing your 9 rental properties, but careful planning and documentation are essential, especially with low-maintenance new construction.

Generally speaking, Boston proper is an appreciation market (low cap rates) unless you have a solid value-add play.