I will also admit at this point we are comparing apples to light bulbs since RentRedi was only costing me $59 per month and DoorLoop will cost $200+ per month and for those that have a lower unit count and only need basic services the RentRedi cost should outweigh the beta tech.

Should I be looking at markets with a lower entry cost? 

I hate to say this, but if you want to get a job with Yardi as the main software, you will need to start at the entry-level accounting.

That would be the lowest barrier to entry in most scenarios. 

Going direct saves you and the seller money, giving you a lower cost to entry which helps all your numbers, but you have to put in the extra work to find that deal.

What entry point do you usually do business in?

@Gabriella Swan, with your management experience already in place, house hacking seems like a perfect entry into real estate.

Compliance items such as adding smoke detectors, hand rails, fire resistant garage entry-door and new stairs outside.

Keep your records contemporaneous: in other words, log your time entries as they occur.

When it comes to managing your mortgage, most homeowners are familiar with refinancing as a way to lower monthly payments or take advantage of better interest rates.