I'm looking at monthly cost to seller vs. anticipated rental income, purchase price relevant to the ARV of the area and interest rate, balloon, etc.

Hey Cameron, for experienced investors I can lend up to 100% of the purchase and rehab costs on 1-4 unit properties.

In the next 2 years, I'll be looking to purchase a MFR to househack. with the idea of reinvesting all of the cashflow to help scale.

I use pricelabs on all my listings and have really enjoyed it. 

Quote from @Brandon Le: Your first purchase could/should be a house hack.

At some point, the juice isn't worth the squeeze for us and we just want to enjoy life. 

Is it better to have a willing seller and buyer before sending the initial purchase/sale agreement?

The substitute of collateral was more of a scenario where you sold for $155K, and instead of paying off the $88K loan in your scenario, those funds stayed at the title company and were used on a cash purchase happening nearby in date. 

Purchase price: $355,500 Cash invested: $75,000 Rental Property near community college What made you interested in investing in this type of deal?

I've not yet invested in my first property, but I plan to purchase my first one by the end of 2023.