@Joe Cantanzriti How big of a project do you think your family can endure? I have seen some pretty dramatic transformation in that area by flippers that gets some deals from the MLS. Usually properties with the potential to pop the top entirely plus some layout changes for you to value add.
I believe a good work order mechanism doesn't always have to involve technology. The most important consideration should be the flow of information. What should the tenant do when there's a problem. (Call? Text? Email? Who should they be contacting?) What should this next person do? Do you need to approve the quote before the work gets done? Is there an amount they may just go ahead without checking with you and send you the invoice when it's complete? Can the handyman fax you the invoice if they can't work with emails? I recommend drawing out a flowchart of how things should go from beginning to end.
With the money piece, I can think of a few more options that may be worth exploring depending on your situation. Talk to some lenders and see if they can come up with anything else creative.
1. Can you & should you leverage against your existing investment to purchase the new place? What would that look like?
2. Would you be able to BRRRR it as if it's a flip and then refi to a traditional loan when all is done? What are the risks if the project drags on?