2-4 units are going to be vastly different than 20+ units.  

We have a 1/1 so it's sufficient since we usually only have 1 guest at a time, occasionally 2.

If you have good credit and sufficient income, that might work.

People are VASTLY less likely to lie on the commercial side, and they don't do the "waive all contingencies" stuff, so it's a lot safer to take the listing broker's numbers at face value.

The vast majority of buildings will allow you to self-manage (AirBNB/VRBO) or use a third-party management company to oversee operations. 

While I have sufficient capital to undertake 1 or 2 flips at a time, the high cost of properties in the DMV area makes scaling challenging without resorting to interest-based financing.Is this feasible, or is it a stretch?

I’d like to again thank you @Nicholas Aiola for being so helpful and generous with your vast knowledge!

I wholesale the vast majority of my deals and market direct to motivated sellers using direct mail, and online advertising, which enables me to find highly discounted properties.Funding: A private lender loaned me $57,000 in private money at 12% and 2 discount points secured by a 1st mortgage.

@Arthur LeaoThe Roth IRA likely does not factor into your strategy as you have described it.The Roth IRA is not sufficient to purchase a property outright or with a non-recourse loan.The Roth IRA cannot be combined with personal funds to create a deal, since it is not sufficient to do a deal on it's own.It sounds as if you want access to the income.While an IRA may invest in real property, doing so is a way to diversify the IRA savings, not a way to bring that IRA money into your real estate deals.

The contingency inspection was sufficient for me as a buyer.