That said, one size doesn’t fit all—and I sincerely hope everyone finds the path and teacher that works best for them. cry harder boi.

Then, between you and your CPA/tax professional you will be able to make the best decision about how that fits with your specific tax situation.

It’s not true frontage, but access is solid and surrounding uses are mostly neighborhood retail, entertainment, and service businesses.Zoning: Commercial / PD (flexible, but vague)I’m thinking through highest and best use for a site like this—especially uses that:Don’t rely heavily on street frontageBenefit from nearby retail activityBenefit from proximity to the highwayWork well on smaller infill parcelsEarly-stage ideas so far:Medical or service-based commercialSmall flex / light industrial / contractor-style spaceAppointment-based uses (fitness, childcare, training, etc.)Other creative infill concepts I may be overlookingWould love input on:Uses you’ve seen work well—or fail on similar rear-located commercial sites of this sizeWhat you’d underwrite first if this were your dealAppreciate any real-world examples, lessons learned, or contrarian takes.

Here’s a quick shortlist that fits your needs (3 doors):Stessa - built for small portfolios; auto-tracks income/expenses and lets you scan receipts via the mobile app.Hemlane - end-to-end PM: leasing, online rent, maintenance, accounting; good if you want workflows plus optional local agent help. hemlane.comBuildium - more robust if you plan to scale; solid accounting and document storage/e-sign for leases and notices.DoorLoop - all-in-one with straightforward pricing as you add units.

DSCR programs are usually the best fit for a cash-out refinance on investment properties.

First, it’s important to make sure your tax strategy fits with your overall financial picture and current income streams.

But it sounds like Milwaukee might fit your buy box as well.

This property showed clear resale demand and a strong pricing gap, making it a good fit for a quick-turn strategy focused on execution rather than construction.How did you find this deal and how did you negotiate it?

I actually own a duplex there myself and have helped other investors navigate the area so I know it fits your criteria well.If you ever want to compare notes or chat about the market feel free to reach out.

I’m happy to share a few things I’ve seen work well when evaluating management companies, along with questions that can help clarify whether their systems are a good fit.