It’s clear that the evolving market, especially post-GFC have shaped your perspective, and you’ve outlined some valuable points about the flexibility and challenges of private lending.The flexibility in ARV and LTV is such a huge advantage, especially for investors who might not have traditional financing options.

Challenges?

@Mindy PerryReally doesn't matter what software you pick as long as it has the features you want.Two biggest challenges with ALL software:1) None are perfect, so deal with the tradeoffs2) Most users rarely put in enough time to really understand how to utilize the software.

I hope this improves.S8 can be a challenge.

Challenge each number. 

Quote from @Sean Barnebey: This is an interesting opportunity, and it sounds like you’re approaching it wisely by considering the numbers carefully.

Really the main challenge is going to be making sure that your wife understands what she needs to do to document her hours and activities.

Challenges?

Yes, having tenants pay ACH via a Tenant Portal software is best, but not all will cooperate and some will play games that result in NSF charges.We allow tenants to deposit cash/check/money order directly at our bank into our account.Many Class C & D tenants have challenges adapting to unfamiliar ways to pay and is often not worth the hassle (and possible evictions) to get them to change:(

Property values here have a steady history of growth, making it a reliable market for long-term investment.2.Tenant-Friendly Laws: While this might seem like a challenge for landlords, tenant-friendly laws create a stable rental market.