I would add to those questions the following:Do you have any reports such as highest and best use, environmental, etc.Are there any known pertinent factors such as close to a dump, sewer treatment plant, airport flight path, train tracks, etc.Make sure you check with the fire department to see if the parcel has fire hydrants close enough, if not, do you need to add and how many and does the current line support the addition of more hydrants.

At least the last half decade has proven this to play out.. compared to cash flow were hey we are going to do this and gambling that rents go up and that cap rates stay low and credit will be where it is today and then in 5 to 7 years if everything aligns we exit.the pros on those of course is tax treatment and income as you hold and pretty much every syndicator out there will take a 100k investment. 

Managing the tenants just isn't a huge added time commitment or expense on top of maintaining the entire property.Second, unless you are a real pro (in which case, you are probably beyond needing to house-hack), it will be pretty darn difficult to hide that you are the owner of the property as you'll show an obvious interest in the maintenance and correct treatment of your home.

I would not incur the expense of termite treatment until you have evidence of an infestation. 

We are expecting a termite treatment at our 4-plex.

Regulators don't like special treatment, banking is about serving the public and community not special pockets of a local economy.I suggest you set your business plan along conventional lines of thought in compliance with the norm, not exceptions to the norm.

The owner's long term capital gains tax treatment was denied and the sale was deemed to be sale of dealer realty (a flip) even though the holding period was more than ten years.

There are some fractional owner products that are designed to help you in situations like this like Delaware Statutory Trusts and TIC products sold by broker/dealers and syndicators that qualify for 1031 treatment and can help to ease some of these timing issues but you'll still want to make sure you have good guidance and keep an eye on your timing.

Qualified Use means that your relinquished property or properties and your replacement property or properties must be held for rental, investment or business use in order to qualify for 1031 Exchange treatment. 

You get very favorable treatment as far as loan terms (compared to a typical investment loan), you'll probably really cut down your living expenses (so you can save for the next downpayment) and you'll get hands-on experience.