This tenant has historically had issues with management being on site for any reason and always insists on being present.  

In the simplest form, you can look at long term historical pricing to see if/how long/how steady the history of price and rent appreciation is ... there WILL be some fluctuation as RE is somewhat cyclical and nothing ever goes up in a straight line always, but does the neighborhood and surrounding neighborhoods have a long term track record, spanning several up/down cycles of appreciation and rent increase?

I really feel every year is a new historic flood here.  

The property is 68 acres and about 1,000 ft from a large river and has a Riverview hillside running through it.It is roughly half wooded and half cleared land with gravel roads accessing %65 of areas.The property has city water, electric, and gas at the road.Land was Purchased by Current owner in 2013 for $1,930,000.The County Assessment Value for the Land and Improvements combined is $2,182,900The land is in 4 Separate Parcels all on 1 deedThere are currently nine structures including a 15,000 SF basketball arena, a historic home with commercial kitchen, a newly built indoor horse arena, 3 dorm buildings (~3k sq/ft each), a 2 car garage and a few small sheds on the main parcel.The owner said he would sell it for $600k cash right now, but my father in law seems to think he could get it down to $500k.$1.9M land for ~25% leaves a massive margin.

A letter from you highlighting the positive features of the new home you find attractive (bigger yard for my dog, another bathroom for my teenager, etc), paired with evidence that you did in fact historically owner occupy for a year (old utility bills, old mortgage statements, old paystubs, etc, addressed to your then-current residence work), would make it pretty rock solid, but this is still ultimately an underwriter judgement call.Because preapprovals are not property specific, they can never incorporate this, so it's on you to set yourself up for success on this front.

Hey everyone, I've got a potential listing to give away in North Port AL right by Tuscaloosa in the historical district.

As a hedge against future-current prevailing market rates returning to historic norms of 6.5% to 7.5%.

Is it really this difficult even if it is not a 'historical' property?

And (2), the historical data you can mine from the MLS seems to be far superior to public sites like Zillow, RedFin, etc.

On my most recent acquisition, the lender used my historical monthly student loan payment when considering DTI.