Real estate has the 1031 exchange gift and the many write offs that makes it preferable for many people.

Massachusetts is not the easiest to evict and the process can be long.  

The important language in your reply is "on their behalf" -- redirecting the principal's funds is not acting on their behalf.Seems to me the smartest/easiest way to deal with lender escrow accounts is to have that feature eliminated from the loan ASAP in the subto process... preferably immediately after an annual tax disbursement reduces the account balance to a low point.But yes, when the principal dies so does the power.

The easiest way to think of the draws is like a reimbursement where after you complete work on the property, the lender sends out an inspector to confirm that work has been completed then gives you funds according to what has been done.You should be using a lender for the purchase as well since purchase and rehabs offer the highest % of purchase price.

A new loan officer or one not familiar with DSCR might offer you the best interest rate and fees on a DSCR loan because their pricing engine told them, but your specific scenario may not fit. for example, a deal I am currently working, First time investor, First time home buyer, living rent free, seeking 80% LTV purchase, Using Short term rental income to meet DSCR, with gift funds. 

My understanding is that a gift cannot be used as a down payment for an investment property, so my thought is to wait 2-3 months before applying for a loan, to season the funds. 

Using a private lender would probably be the best and easiest option in this scenario. 

I think you missed;1- easiest and fastest way to sell their property 2- qualified buyers when given the opportunity of buying via seller financing won’t tie up ability.  

Starting with a turnkey is certainly the easiest first step for OOS investing but it all depends on your strategy and goals.

But what do you call an interest free loan that you never have to pay back ---- A gift!!