So the biggerpockets support staff got back to me and said they're working on it (this was Dec. 4) but I haven't heard back from them and just checked and it still doesn't have that functionality.I've just advised them that I've had to cancel my regular monthly meetup because I couldn't use their event scheduler. 

Or would it be best to get a conventional loan and charge regular rent to cover the mortgage?  

Pets with a pet fee and/or an additional security deposit for pet could make a lot of sense.7.

At this point, I don't know enough to take on the independent lifestyle, so I think it would behoove me to work for an employer to gain knowledge while having more security.

Assuming tenant passes critieria, email them to notify and invite them to sign up with Cozy to make security deposit, and ask that they call electric company to move bill to their name.

Should I be requiring a security’s deposit from the seller and soon-to-be tenant as well?

I always recommend a legal professional - you can ask questions and though they are more costly, should provide you with the answers you need to feel secure. 

I'm an investor in Massachusetts and I'm curious if there's a creative way to set up the landlord/tenant account that holds the tenant's security and last months rent deposits in such a way that the annual accrued interest can be paid to the tenant automatically...As of right now I'm required to manually send a check to each one of my tenants on their year anniversary.

Therefore, you father (the executor) will need to work with the IRA provider in having them update the your uncle's IRA to list the name and social-security-number  of the beneficiary of the estate (not your uncles name as he simply the executor). 

Assuming you have a decent job and reasonable credit score, you should definitely be able to secure better terms through regular conventional financing.