I met with the guy in person the weekend after and asked him to give me a more detailed estimate (at least the high ticket items).

I'd bring these items up, very gently and kindly ask that you be granted a waiver - you lost a lot of money when they told that you couldn't rent years ago when in fact, maybe you could have?

Many different factors that will effect all the items regarding the deal as you can see.

This can truly be put to the test when it comes to counter offers and negotiating repair items after an inspection.  

If the personal decision suggests staying, you can do the same on your existing home...refinance or get a HELOC on purchase a rental.In many cases, your existing personal residence does not make as good of a rental investment as many other properties would and limiting your potential investments to one property (i.e. your existing residence) is, well, very limiting.Good questions and nice work on kicking these items around.  

I set up Amazon subscription items to be delivered to the hotel and they restock our supplies with them.

Check to see if any major expense items are coming up, and they have sufficient reserves. 

I  also thought that the insurance, taxes, as well as the current leases can be figured out during the buying process/due diligence and that something can be put in the purchase contract regarding what to do with those items going forward.

This will teach you enough about your local markets to start answering your own questions on where to invest as well as give you food for thought on what you are trying to achieve with investing (what kind of investing, your criterea, etc)Good luck

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