I know that we need to look at obvious needs for repair, get both income and expense statements, copies of leases, etc. and that we should have a professional inspector to uncover any potential surprises, but before even all that, is there anything in particular that you are looking for that you consider immediate red flags when you assess your investment options?

It sounds like you are trying to shove a square peg in to a round hole.

So, for example, if you had paid your mortgage down by $30,000, you'd walk away from the sale with a total of $65,000 in your pocket ($35,000 from appreciation + $30,000 from the equity you built by paying down your mortgage).So my Question is does anyone see this as a Red Flag or any concerns going this route to build my second house on my property?

Moreover, if the seller is resisting having the utilities on, I'd view that as a HUGE red flag (similar to how I'd view it if someone tried to sell me a used car, but wouldn't let me test drive it or even start the engine).Since correct and thorough due diligence is the foundation of successful REI, I'd be extremely hesitant to buy a property without testing the aforementioned items (unless the property was so heavily discounted that I could replace/fix all of those items if they turned out to be faulty...but even then, I'd be wary).I'd suggest strategizing with your agent on the best way to get the utilities turned on so you can do a correct inspection...Good luck out there!

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

I am looking for 3 or more acres to build a 40k+ square foot structure which will serve as an events space business.

As for the rent, according to Rentometer, there are currently identical apartments (same bed and bath count and square footage) in the same complex being rented out for $1,650 a month, so I think $1,500 is a bit below market price.

And since they’re already in the process of being transferred to a nursing home, they’re unable to gift the property without raising red flags.

If you accept rent even partia you go back to square 1!

Find properties of similar characteristics (square footage, garage, pool, fenced yard, etc.) and also look at when it was sold (3 months, 3 weeks, 3 months, 3 years?).