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Your property manager just doesn't want to do the extra paperwork.

If I want extra protection I then place that property in my LLC.EVERYTHING is not in my LLC.

But the extra amount you purchase is additional depreciable basis.The $50K you refer to as your carried over basis continues to be depreciatedThe $100K of profit isn't depreciable because it's not real estateThe $10K of purchase over the amount of your sale is depreciable with it's own depreciation table.

I really like my Realtor who is super professional and does what he says he's going to do and goes the extra mile.

Start with the highest interest rate card and cut any extra spending and put your money towards the debt.

What are the advantages of purchasing a property that needs some extra love put into it vs purchasing a turn-key STR property? 

Plus the big guys have more experience negotiating with municipalities for extra incentives to build valuable housing to replace low-income mobiles.I guess it would just come down to your goals, short, medium, and long-term. 

Having to wait an extra day or two to get your general on site may be all it takes to miss out on a deal.

We had a few contractors try to pull a few fast ones on our SFHs when work was done (overordering and then walking with the extra materials).