I've have my agent make sure each property allows STR.

One thing I did notice is that almost everywhere seems to allow pets so that may be something to consider if you haven't yet.

That will allow you to quickly analyze deals simply based on the purchase price and the total potential rent, without having to calculate every single cost for each property.

Make sure their deposit and first months rent payment clears before you give them keys or allow them to move in.

We will have approximately $50k cash available when we are planning on buying which, in an area like Boston wouldn’t allow for much.

Designing a platform to allow people to interact is not, to me, a useful goal given all the other platforms out there.  

Most lenders won't allow you to put it in and LLC, it needs to be in a trust or your personal name.I'm no attorney but I've never worried about being in an LLC too much when it's not allowed by lenders, I just make sure I have the right structure and insurance. 

Found a local company that allowed 401K/IRA's to be rolled into one of their real estate investment funds.

Here in LA, we're allowed to build studio apartments out of our garages (they're called ADUs).

When my health insurance became $1200/month I got a job as a direct support staff at a group home on 3rd shift which has lasted about 15 years and has always allowed me to have many hours per shift to myself to focus on my real estate and learning things.