@Brian FournierEvaluate it as a business, because you are buying a business and not a building.As a business it is valued by the cash-flow it produces and the rate of return generated by the business' growth.I would learn your target area intimately ... to the point where you know not only the market median rent, but the first two standard deviations and the expected economic vacancy range .. and how it is going to grow (or not).   

At this point in time I had never had to deal with a neighbor like this guy.

It will pay itself off in time.

We are based in central Iowa and are considering a move out of area, at some point in time.  

An additional charge of $25.00 per person per night for guests older than age 2 will be assessed for parties larger than 6 people.If your party is larger than 8 persons please contact us. 7.Check in times: You can check in at 4 p.m. on your check in date and check out is at 11 a.m. on your check out date. 8.Minimum Stay: This property requires a 4 night minimum stay.

See which ones are possible in your exact personal situation at this point in time.

I’d like to, in time, build 3 quadplexes on the land and rent out the units.

I'm not your lawyer and this is not legal advice, etc.IF YOU STAY IN WASHINGTON, WATCH OUT, BRO.A 2-second google search showed me that Washington state recognizes some sort of nonsense called committed intimate relationships, which means that if you and your girlfriend live together and split expenses, she may have a claim on all your property, even if it is 100% owned by you and even if you do not hold yourselves out as being married.To avoid this, you will need to enter into a cohabitation agreement with your girlfriend, clearly setting out what is yours and what is hers (for example, all real estate now owned or later acquired). 

(Hopefully they'll change the mascot at that point in time as well).

This will come in time, hopefully.phil