I presume your intention is to be an active investor who owns physical real estate and not someone who invests passively.

Quote from @Nicole Laba: I work with investors in Chicago who are actively buying off-market properties, and Ive noticed that everyone has a different approach when it comes to sourcing deals.

You have to work with someone that is experienced and very active in the field.

The worst thing is to pay for a service where you don't get a benefit.If you have STR's and actively manage them, then there is a good chance that you can treat the propreties as active instead of passive which will allow you to offset the losses with other forms of income such as wages, interest, dividends, gains, etc.

.: HiRepairs were going to be paid for before closing, as the seller having some other time sensitive activities needing to be met, my agent and I decided to grant a seller credit to the buyer for these repairs.

For those of you who actively acquire land, what challenges have you faced in different markets?

Hey Ian, since you're not an active agent I would connect with some local investor-friendly agents in your market.

The other factor that's relevant for me is that my husband is a high end W-2 wage earner and we could greatly benefit from the potential tax benefits of actively managing the property. 

Quote from @Noah Laker: I'm a real estate broker and my client is a high W2 earner, taking advantage of the "STR Loophole"His CPA told him that he can only do cost segregation on properties which are active STR's.My understanding was that, if he obtains REP status through any one of his properties, that he can take advantage of depreciation on any investment property, even if that one is not an STR.

However, if you made the property available for rent in 2024—meaning you actively advertised it, listed it, or had it ready for tenants—you may be able to deduct certain expenses like mortgage interest, property taxes, maintenance, and depreciation for that period.