We will eventually construct but we are not sure exactly. 

Then, eventually, if you keep it up for 2-3 years the deals will just start coming to you.I can't comment on what's "better" when it comes to flipping, BRRRR, etc. because, again, I can't speak to your specific situation.

I want to initially self manage but eventually I’m sure we’ll pass it off.

I think doing this in the next few months would be really good because eventually once the rates come down I think I would gain some equity from the appreciation and then I could refinance and pull some money out and throw it in another deal?

Look the guy above you runs a mini fridge over to their house and they still demand more. it doesn't matter what you do eventually you have to enforce a late fee or tell them "no" about something and you're the evil landlord. 

(Prior to graduating college and getting a full time job, I was an incredibly social person, so this was a huge change of mindset to sacrifice the way I did).And on the other end, my brother decided to start his own business while I was working and did not work hard as he spent money like crazy and eventually went bankrupt (filed 1 year ago) .

Or put the 88k in, refi out of the HML which requires you to come out of pocket quite a bit of money as well, and hold it long term which on paper may eventually make you whole.

I think doing this in the next few months would be really good because eventually once the rates come down I think I would gain some equity from the appreciation and then I could refinance and pull some money out and throw it in another deal?

@Josh Rodriguez, every property wears out eventually.  

This would allow you to eventually plan strategically to move into the new house and convert your current primary into an investment property... to then 1031 into your next project(s).