So for repairs, I recommend you get clear on what items you are likely willing to deal with yourself and then leave the rest to a professional.  

Just count the number of items in a house from foundation to shower glass.

Since this is a commercial deal, your offer should include a provision for “Seller Deliverables” (items that must be delivered within x days after the effective day of the contract.

I obtained an estimate to replace all of the previous items and it will cost roughly $18,000.

Its important to note that you only get to deduct the higher of either standard deduction or your itemized deductions(home interest & other) so if you sell you'll still get the 12,200 married or 6100 single deduction so you'd only lose the difference between your standard deduction and interest on your primary.Example: So how you can see it is if by living in your primary residence you only get 18,000 total itemized deduction then by selling and leaving you'd only lose 5,800 deductions tax wise but like Brandon mentioned you give up appreciation as well.If this is offset by the apprec/amort/cashflow/tax benefits of the new property you're going to invest in then sure you could consider that but its all about your risk tolerance and preferences on investing.

I also found I preferred GCs that would give me itemized quotes so I could pick which things I'd tackle myself and what I'd leave up to them.Right now, I'm considering buying property in the Loch Raven area and since I live in Endor Gardens (for now), I could have GCs quote me on jobs to my own property that I could then get a reasonable idea for what they'd charge for doing the work on other homes in the area.Did you find that GCs gave any kind of discounted prices for investors vs home owners?

that will dictate if you can get higher end tenants willing to pay more for these items and whether local market has competition for central air units.

But you'd also be paying relatively less for your home than if you were to buy a SFR for yourself with no income to offset your expenses.If, or should I say when, you rent out your unit also, you'd be grossing $2,200/month, and there'd be what to talk about (is $1,200 a month enough to cover all those items listed above aside from debt service?).  

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Take a checklist with you and take pictures/video of each item/room to review later.