Note both of these options require paying the tenant to vacate for a no-fault eviction (terrible name as if lease is up it is not an eviction).Note terminating a lease agreement for the purpose of rehabbing the unit is under attack in some places in the county. 

The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

It looks good) I stumbled across someone locally who does it, but I'm sure you could find someone there if you or other out-of-town investors like the idea of paying a bit more for that level of security and obtain a remote monitoring source of the exterior of the properties.

You have to disclose all of this when you sell, so you will end up paying your plumber or discounting to your buyer.

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

One would think that a bidder would pay $45,000 in my example (since they are assuming the first mortgage), but they are actually bidding $225,000.

You might not cash flow right away, but even just offsetting what you were paying in rent while building equity, getting tax benefits, and learning how to be a landlord is a game changer.

Be sure to: call & verify employment references, request pay stubs to confirm income & check rental history by contacting the previous landlords.Keep the momentum going!

So all of the gain and depreciation recapture are initially still tax deferred.However, like Joe said, the down side is later when sold  you lose the 1031 option. the client will pay tax on all gain and depreciation recaptured from before the 1031 also. 

I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.