What i do know is i will convert $300k to roth at an estimated 23% fed this year.  

If your estimated rent from a property pays off the Mortgage + Maintenance + Property Tax + Insurance.

I have some of the required funds in a HYSA, but will most likely need to draw from another account and I'm curious which method is the most efficient in terms of taxes/capital gains, penalties, loan repayments, etc.Based on my previous transactions in the market, I estimate ~$45k cash to close: $20k for the down payment, $15k for closing costs and prepaids, and $10k of starting reserves.

If the rate is reasonable then it may make sense to try to save fast to get to the 3.5% down payment on a double or triple - househacking may allow you to increase your savings rate and pay down that loan even faster.As for estimating costs, closing in NY factor at least 1% of the mortgage amount for tax, plus $1500-2000 for lawyer, title and fees, then the amount required by the bank for escrow will depend on the actual property taxes and insurance.

The property alone is worth a million but is generating an estimated $250k/ yr with the ability to add 3 units on site and acquire an additional 13 acres.

@Erich Hatch, I think having a GC provide estimates is difficult.

It’s a good move to have a contractor walk through before making an offer to estimate costs and timeline. 

I am familiar with rentometer and that is where I got my approximate rent numbers from.

You can use Airdna & other STR estimator tools to get data on potential income/vacancy based on your location and property size. 

If yes then what should his/her credentials should be and "approximate" cost?