I'm sure you understand the "burnout" that comes along with project management, so let me know if I can reduce some stress for you while learning more about your world!

Some people are not able to handle this level of stress, so know yourself. 

A real estate professional is a distinct designation from the IRS and there are certain rules/thresholds to do before you can call yourself a real estate professional for IRS purposes.You may want to factor in all of the above to see what the cost of cost seg will be and what your decreased tax liability will be for 2017 and what your refund will be from carrying back the NOL to 2016/2015.

I'm cool with spending $300/mo to own this kind of asset, I just have to wrap my mind around my net worth increasing as my checking account decreases.

Deferred maintenance is almost always worse than it looks on pre-foreclosures, especially when owners are under stress and pushing repairs off.I’ve found the same thing — assuming worst case early keeps you honest, and getting access (even limited) before the sale is where real clarity shows up.

Sure, you can be comfortable with the strategy itself and its implementation, but we stress the importance of creating a DEFENSIBLE strategy in the event of an IRS audit, allowing you to KEEP the deductions you received and ultimately providing you with confidence when your return is filed.Also, the more detailed your time log is, the easier it is for a tax advisor to review and point out what hours will stick when an IRS agent takes a look at your log.Things you can consider to add to strengthen your time log: Screenshots of time spent on calls with contractors/cleaners/etc.Pictures of work you are completing (i.e. painting)etcChris Tile, CPA

Make sure you have a healthy reserve account per property so surprises don’t turn into stress or forced decisions.3.

That all makes sense, and it sounds like you’re approaching it the right way, especially stress-testing occupancy and being conservative on insurance and cap ex.One thing I’d focus on as you narrow in on the second home loan is that you’re making two decisions at once: 1. what’s cleanest for the deal 2. what’s most resilient for the balance sheet long-termSecond-home financing is often the least friction up front, but it can quietly lock in some constraints around future leverage, basis, and exit flexibility, especially given the insurance volatility. 

.• Start forming the “core four”For Phoenix rentals, this usually means:– An investor-friendly real estate agent– A solid property manager– A lender who works with investor products– A reliable inspector or contractorEven meeting one or two now will make things smoother when you’re ready to make your first offer.You’re doing the right thing by getting plugged into the community ahead of time — that’s often what separates smooth first deals from stressful ones.– Ridge Lending Group (Licensed in 49 states, excluding NY)

Actively participating may allow you to offset non-passive income, and you can also take depreciation, potentially accelerated through a cost segregation study, to optimize your returns and save so you can really scale.Building a local team that you trust can make scaling much easier and less stressful too.