My main concern is regarding cost-basis and future capital gains tax when I ultimately sale the property. 

I have had turns where things are recommended to repair based on the field operator and my property managers notes, and I would expect the professionals with eyes on the property to have the best opinion on when the inevitable concern arises. 

I’ve worked with a lot of first-time buyers, and common concerns like HOA restrictions or property management costs often come up.

In our case i'm very concerned w high transaction costs if we sell. 

I am a rookie investor working on building my portfolio and a structural engineer offering consulting on any structural concerns you have for houses you may buy, or if you want to know out a wall to open up some rooms in your next flip. 

Have you been to any local city council meetings to see if others in your area have the same or similar concerns?

I apologize if I wasn't clear on my question, I didn't really go into my plans for how I would invest as I didn't think it really pertained to my question, yes I know I should not purchase a rental using a HELOC and certainly that wasn't the plan.Whether it be a flip or brrrr, I would use some investment vehicle that would allow me to pay back the money.Roll into as when I purchase my next primary home, use the equity towards the house.The premise of my question was just is owning a home expensive enough now to where it'd be worth putting more money towards it when purchasing to lower payment/pay off quicker, or would it still be worth it to use all of that money towards other real estate. 

In vacation markets, I'd be a lot less concerned about changing rules on Airbnb and would expect stronger appreciation, versus in a normal city.

HelloWe are in the process of trying to lease out our second SFH rental property.  We have previously had a firm no pet policy.  However, we are seeing a lot of interested individuals asking about allowing pets.  Our ...

If you are concerned about lawsuits, an umbrella policy may be a better choice.An LLC is useful for two things: anonymity and legal protection.