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.

I want to make sure they can close these types of transactions and are used to working with real estate investors...

A benefit of this setup is that VRBO still processes payments and handles the transaction.

The analysis also reports that new multifamily development will “remain near the average recorded over the past five years”.Integra Realty Resources’ 2017 Commercial Real Estate Trends Report ranks Pittsburgh #2 on its Top Markets by Multifamily Transaction Volume Based on YoY Change.Pittsburgh’s rental vacancy rate has declined by 25% over the last five years.Pittsburgh is booming with developments (see reference #6), “there is no better place to be a developer right now than in Pittsburgh.

You will have a leg up on the language, transactions, inspections etc.  

Selling the PropertyIf your parents decide to sell, they could: Sell As-Is: At a current appraisal of $350k, they could walk away with a sizable profit (after transaction costs like realtor fees, taxes, etc.).

The IRS views it as taxable income because it’s not being used for the purpose of deferring taxes under the 1031 rules.For example, if you sell a property and only use part of the proceeds for the next investment, the leftover amount (after paying transaction costs, etc.) is taxed.

I think what you’re referring to is a checkbook IRA so you can bypass the custodian when performing transactions/investing and all assets/accounts will be held in the name of a special purpose LLC or Trust which is the instrument that gives you checkbook control.  

An agent told me that 9/10 transactions they handle are cash and not financed - so i think in this particular submarket going in with financing really weakens you.  

Closing CostsMake sure you also budget for closing costs, which are a collection of fees and payments made to the various parties involved in your transaction.