This is a house that I’d tell others to run from, but since we already own it we’re just trying to determine best options.  

The discipline to run on a budget for a number of years or decades depending on your math, doesn't factor in emergencies or market changes where the HELOC could be used to invest in other places.

I also use their virtual credit cards which enables me to assign a card to a specific person, like the cleaner for my STR for example, so when she runs a charge, it automatically drops into the right account in terms of categorizing my expenses.

This is what I am encountering, in the current Mortgage Industry.If you think you will go FHA, Conventional, FHA 203k, etc. and then Quit Claim the property, to a LLC, or a Land Trust you run the risk of the lender discovering a Title Transfer occurred and activating the "Acceleration Clause" or "Due on Sale Clause" that requires the loan to be paid in full, within 'x' number of days.

Run the numbers.Would you rather wait say 5 years to buy a $350,000 home at 3% versus 6.5%.

At the very least, let it run for a year or two and see how it goes.

The issue you are gonna run into is you will not find cashflow in DC you will find appreciation and cashflow after 5 years.

As a licensed real estate agent and contractor, I speak the language and can guide you through the process to ensure everything runs smoothly.

This is the simplest method, but it also means your tenants are more likely to abuse the utilities by leaving windows open with the heat or A/C running, leaving lights on, ignoring the toilet that constantly flushes on its own, etc.3.

That being said, anything can happen, but if you run your numbers accordingly, make sure that your contractor is trusted and do all the other stuff you'll be a little more protected than the next person flipping that does not do this type of calculation.