I have an STR we've run for about a year.

This tends to be more time intensive and more for someone that has a lot of time and limited income as you may find a "home run" type deal with some effort/energy.

This rule is good for the 30,000 foot view of running numbers on deals so you do not get bogged out with running those numbers on every single deal for example..

Run don't walk

We are all running our own race!

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%.