its been a lifelong dream of mine to be in ann arbor

Has anyone been through the experience of taking over a property and having to remove a tenant to fulfill the duties of the requirements loan?

Fulfillment by Amazon.

You can get a great sense of the vibe in an area via social media.I was a lifelong San Francisco Peninsula resident and did all of the above when investing in Austin.

that's all I have done my entire adult life since I was first licensed at 18.. there is a difference in being a retail real estate sales person and using a license to further your investing goals.Its not an easy business by any means to be a retail agent and there is a high burn out rate.. not as high as wholesalers but its at least 50%...If your an ACTIVE investor I cant see how you can do without it.. if your fix and flipping in my mind its mandatory.its about 2k a year to keep sometimes less and If your business does not allow that or like some say the cost is to high then in my mind your not really in the business its a pittance to spend to have access to all the info and be in the club.if your goal is to be a lifelong landlord then work for a commercial brokerage that specializes in cash flow real estate just being there will open up doors.if by chance your very good at sales and have a very large warm market you may shock yourself in how much money you can make just in transactional real estate.. 

After that, you've fulfilled your occupancy promise and can move out, converting it fully into a rental. 

typically, contract law dictates that agreements for one year or more must be executed in writing. an email response is likely not enough to fulfill the requirements of an executed contract

Is it random or is there a plan you are fulfilling with the 100k per year?

This, in my opinion, is what I believe will be more fulfilling for my life and it would give me a sense of accomplishment.

But like all have said previously there is nothing wrong with renting out your property you have purchased with your VA loan as long as you fulfil your owner occupied time frame.