It sounds like you’ve navigated a lot of different scenarios and made strategic decisions based on the circumstances.

The last thing you want to do is push something in and get it declined due to an unforeseen guideline.

@Adria T. the PM company has to communicate, get a tenant in quickly and be able to handle items that are unforeseen..

I thought DSCR could be the answer and planned to rent it out until I was able to qualify for a conventional so I could move in as my primary, but unfortunately it didn't work out.Very specific circumstance, but thought it was worth mentioning!

Start-up costs are also deductible but are amortized over 15 years with a limit of 5k.Start-up costs have strict rules and your case might not be the same as this one.Case Summary:Timeline line of eventsStarted investigating property: FebPut first contract (canceled): MayBought first property: December 30thWhether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business:Whether the taxpayer undertook the activity intending to earn a profit;Whether the taxpayer is regularly and actively involved in the activity; andWhether the taxpayer's activity has actually commenced.On the basis investor testimony, we may assume that he undertook this activity to make a profit and that he regularly and actively engaged in it.

Also, it depends on the circumstances of the investor.

They can provide tailored advice based on your specific circumstances. 

Sometimes there’s extenuating circumstances that may make buying a net $0 cash flowing property worth it.

Issues like contractor delays, supply shortages, or unforeseen repairs can extend your timeline, which adds to your holding costs (mortgage, utilities, etc.).Tip: Factor in extra time for delays and have a backup plan to stay on track.Over-Renovating: Many new investors fall into the trap of over-improving a property, especially when they try to bring in their own taste.

We don't provide tax services (just bookkeeping/CFO) but are huge fans of receipts in all circumstances just in case...