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.

I have fully paid off my primary residence and have secured a HELOC of $435K against it from US Bank, secured a month ago.

Fortunately, you have the security deposit if it comes to that point to help cover some of the costs. 

That's both halves of medicare and social security, so 15.3% in total.

I want to secure some information on co-wholesaling. 

I'm curious if you the spreadsheet file you used is one of the ones available from here in the Bigger Pockets files section.

If I want security I would leverage my property 100% and put the cash value in a income fund.

Anyways, I was talking to our conventional financing lender about this next step, and she mentioned that unlike new residential loans, their company won't be able to use the income from the leases on the new apartment building until we file our taxes in 2019, and then they would use the income from our Tax Statement.