If you want to buy a villa/house, you have much less choice.

The power of leverage is one of the main benefits that distinguishes RE from other investment choices, and the refi is where real wealth is made.

Is the information about “In MA, tenants generally have 30 days to pay repair costs...” available somewhere online? 

Review their online financials/annual statements.

I just looked online and saw that in Seattle for months to month lease the landlord is only required to give 20 day notice.

In my experience, most of the online calculators are just taking an educated guess for you.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Lease options are the vehicle of choice here, until I sort out how to get to the other side of the ceiling imposed by debt to income ratio.

It seems you are falling for the alarmist rhetoric you’ve been reading and watching online.

The majority of buyers appreciate the expertise that a good agent provides (local market knowledge that can only be gained by being active in the market buying and selling all the time, looking at most of the new listings in person or at least online daily, a background in or at least understanding of building construction, relationships within the network of professionals in the industry doing deals, vendor referrals, legal protection through E&O insurance and keeping up with constant changes in approved contracts and required disclosures and forms, negotiating skills (the average person is terrible at negotiating directly and has no desire to, I find Americans are uniquely averse to negotiating and prefer to outsource it but I digress), etc.).