The way I’ve been approaching it is by underwriting markets the same way I underwrite individual deals — looking at taxes, rent-to-price relationships, tenant demand, and how forgiving the area feels if assumptions don’t play out perfectly. 

Got it — that flexibility helps.If courthouse steps are your core lane, one thing I’ve seen work is having a secondary acquisition channel lined up (off-market or MLS value plays) so capital isn’t sitting idle while seasoning plays out.Are you mainly focused on a specific county, or just wherever the numbers make sense?

However, the properties in question were condominiums, and it might have played a role.

My humble advice to anyone attempting to do creative finance is:Creative finance is for experienced investors who have access to capital if anything goes wrong.Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal levelLearn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are neededKnow everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

However every city plays by its own rules and you must be aware of them.Because you’ll be operating from Virginia, I’d also recommend talking to a few STR management companies while you’re in town.

Even though the cost to build might have gone up (appreciation); the value will go do down if you don't keep a comparable lease in play.

You can always come back to coastal appreciation plays later once the portfolio is paying for itself.

Guest experience, management, and seasonality all play a role.

Some lenders fight this but it's worth finding ones who will play ball.What market are you flipping in, and are you managing the project yourself or have a GC handling day-to-day?

Poor planning and mismanagement has played a big role.