The free service, for landlords with two or less properties, tracks expenses, profit/loss, etc. of your rental properties ($50 fee if greater than two) but it requires linking accounts in order to automatically track and categorize expenses for you.I’m always uneasy when a website requires linking bank accounts.

The other option is to do a non agency product, such 12 months average bank deposits or asset depletion or DSC (debt service concerage) where 90% of the rent covers your total monthly payment 

(opinion bonus) Is it worth the extra $2,000-2500 to hire two attorneys in two states to set up these LLCs/OAs versus utilizing some services I see where it can be set up for about $200 each if you add in EIN/OA work and maybe $125/year for registered agent in that state?

By the way, if you feel the need to save a few dollars, many Property Managers offer a service where they will market the property, handle showings, screen applications, and get the tenant moved in then they hand it over to you for on-going management. 

Make sure it explicitly explains the process for termination if you are unhappy with their services, but especially if they violate the terms of your agreement.3.

There will always be debt servicing costs which each type of funding.In using the drawn funds from a HELOC, you can follow the exact same procedure as your example #4..couldn't you?

I mean you have been doing it already and since you can cover you debt service buying an house that will provide you two additional sources of income if you can make it cash flow that can also help you pay off your current debt, and as you pointed out you would also have a long term asset that should reasonable go up in value as well over time.

Be a service to the seller and make a connection.

This has historically been a difficult property to rent, and it has been vacant for 2 months, with no other qualified applicants at this time.The applicants have 2 small "service dogs" with certificates from a random website. 

Home 365 is a new subscription based home maintenance service created for landlords and property managers.