If not, even though you are a re pro, losses are passive & deductions are limited.There are 7 scenarios that will qualify as material, and you only need to meet one:*500 hours*Substantially all participation*> 100 hrs and at least 1/2*Significant participation*5/10 years*Personal service activity w participation in last 3 years*Continuous participationTo materially participate, you must be involved in the operations of the activity on a regular, continuous, and substantial basis.Once you pass the pro test, the material participation often comes along for the ride.You can elect to aggregate all rental real estate for purposes of measuring material participation under Sec. 1.469-9(g).Your time spent on all your rental properties (STRs don't qualify) counts as one activity, making it easier to materially participate.In order to make a strong case with your CPA and the IRS you need to document your hours.Best practice is an hours log where you are as specific as possible.

My advice probably isn't the one that will maximize your return, and it may not even be what I will follow as we continue to grow our portfolio, but here it is.My wife and I manage 5 units (4 we own, and 1 we arbitrage), and we allow anyone to give us 30 days notice to vacate at which point they can be let out without penalty.

That said, I prefer to use a HELOC for short term investments like fix & flips because I only pay for what I use and I can continually keep recycling the money.

Colorado Springs is a beautiful place to live and will continue to attract new residents from all over the country for decades to come! 

@Jonathan Greene infers from your use of the term "lease" that this tenant started off on with a lease for a period of time such as 1 year and then when the lease ended no new lease with signed and the tenancy continued as month-to-month under the original lease terms.

Also, solar companies typically continue to raise their fees in the contract each year it is owned.

A business/way of life to continue? 

Those people overlooking what it means to “materially participate”Here’s the Material Participation Criteria:Spend more than 500 hours on the short-term rental businessDo substantially everything for the STR businessSpend more than 100 hours on the activity and no one other individual spends more time than you doSignificant participation activity for more than 100 hours, and your combined activity in all significant participation activities exceeds 500 hoursParticipating in the business for five of the 10 previous taxable yearsPersonal service activity (non income-producing) for three of the previous taxable yearsRegular, continuous, provable participation in the business for more than 100 hoursA Cautionary Tale: The Story of JacksonLet's take a moment to learn from the mistakes of others.

Biggest take away is permitting timelines continue to increase!

If you’re willing to continue to do the bookkeeping yourself, there’s several wonderful options on courses you could take for learning how to do RE bookkeeping.