I think spending some time and resources on learning the House-hack or Flip strategies would be a game changer.

If you are going to focus on listings only list ones that are priced well to sell before spending your money.

You will also quickly learn how to manage properties well instead of spending decades figuring it out like most investors.

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

I have a W2 and can survive off it, so I never really needed my RE profits to spend on myself.

So, as a buyer I would not want to spend money before having a contract.

Don't spend the check until it clearsRegulators do not view investors as being altruistic.

Also, how much time do you want to spend doing real estate vs. your main job or extra work in order to fund it.

If I was in your shoes I would find ways to streamline your day job so that you are not spending as much time in that role.

There are a lot of inconsistent contractors, so really spend some time vetting them.