We're spending so much money...this better work feeling."

I wonder if the disciplined, long-term play is better than having the cash now.

I would love to connect and get a better idea of your rental strategy and see if I can help!

I found it better to source a renter myself.

What is better for me to work with you?

Quote from @Will Greenlee: I would agree with @Drew Sygit every software has its kinks and this one along with all the other ones started somewhere.. 7-8 years ago Buildium was less effective than it is today, and now it is a lot better.

You want to be careful not to bite off too much on a first purchase so maybe if more four units or less or available that could be a better starting point with less risk and more ability to learn without potential loss.

I had a better feeling about this contractor so I hired them.

My ultimate goal is not using my savings during this process, because I want to train myself from the onset to think creatively and not deplete my reserves instead of finding a better deal or more productive relationship.

Highly recommend you start getting sample contracts from other PMCs to evaluate what yours may be missing.Then, you may be able to renegoatiate the contract with your current PMC - or move to a better one.