However, you can likely sell all the properties in the required timeline to do the 1031k, although that will take some effort/cooperation between multiple buyers/brokers, considering the separate markets.  

It may not be required, but we are generally in a better place to absorb the loss than our tenants.

Short term rentals do get more money, but also cost more to run and require more time.  

@Kyle Cross you claim to know a lot about the industry, but your questions are vague and so is the info you've provided.Not sure how managing 8 units doesn't, "require much management"?

We review yearly with our CPA who files the necessary forms.By law, IRAs require a custodian.

Because of my savings and lack of expenses, I'm in a very comfortable position to make my first move, but because my income is mid, I'm unable to meet the Debt-to-Income requirements to qualify.

If it’s tied directly to the lender as part of your mortgage agreement, you’d probably need to negotiate with them or refinance with a different lender who doesn’t require that restriction.However, if the restriction is part of the property deed itself and was placed by a previous owner or another party, it can be more complicated.

Most lenders who order appraisals are required to order them through a 3rd party AMC, which can add additional costs to the appraisal but ensures that there is no lender (Or borrower) bias in regards to the values.

What kind of seasoning is generally required as it relates to the rents/revenue as it relates to servicing the note, etc...I currently own one PadSplit (acquired via Subject-to) that has been up just over a month.

This apartment required a cosmetic renovation that is going to run me around $27,000 to redo.