I was approached by people who are interested in leasing my property long term and use it for cooperate business travel accommodation. 

https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

Not having done your 2023 return will in all likelihood 'hurt' you somewhat in the short term because lenders will want to see it.  

First unit lease is up for renewal on 10/31/2024 and has a good long term tenant.

Faster approval, more flexible terms, and less stringent qualification criteria.Tip: Establish a solid relationship with private lenders and clearly outline your investment plan to gain their trust and secure favorable terms.

I'm gonna tag @Elise Bickel Tauber in this post as she's definitely the right person for you to get in touch with in terms of investing in the Pittsburgh market - smart move by the way. 

I know if card X is charged, it's the cleaner at my North Carolina short term rental, for example. 

@Eryn Garcia  I agree with @Eli Kantor  the hot tub instructions with photos really saved us a phone call at one short term rental and that is saying something since my husband can figure most things out. 

Have a legal advisor or counsel review your documents before signing.These will make your ultimate exit strategy, post Hard Money financing period, much easier when: - preparing & submitting paperwork for individual tax returns - maintaining the note in good stating with consistent payments & digital payment history paper trail - digital and/or easy access to documentation - preparing for a Re-Fi, Conventional financing, payoff, or even Flip/Sale & deed/title reconveyance to remove the Hard Money Lein holider at the end of the note's term

This is common in my area/Colorado in general especially the ski towns that still allow short term rentals.