Up until that point the property was solely in my name.If I decide to occupy the property after 2 years, and decide to sell the property after 5, do I owe the full deferred tax amount, or are the taxes "prorated" based on the ratio of time the property was investment/primary?

I would invest in a base model Sundance or Jacuzzi brand.  

Shared housing provides affordable, flexible rental options for young professionals, remote workers, and students.As shown above, co-living properties have more demand than traditional two-bedroom units and appeal to a wider tenant base.2.

I know getting my real estate license is one option, but I am looking for more than one option.I am based in CT, so if anything specific is coming to mind let me know, open to all Ideas.

I am based in IL just outside of Chicago.

However, I am also considering duplex and tri-/quad-plex assets if they pencil.Additionally, I currently work for a locally-based commercial developer/lender on multifamily, land, and some hospitality projects.

You need to remember that, hopefully, this is a long-term play for you, so work with a trusted STR designer (I have great recommendations), and spend the money upfront so you can be the most successful in your area.

For instance:If your area has many corporate offices or conference centers, you're likely to attract business travelers.Family-friendly suburbs with parks and schools often attract families.Downtown locations near nightlife are popular for groups and parties.Review Competitor ListingsSearch for successful Airbnb listings in your area and study their target audience based on:The language in their descriptions.Their reviews (guests often reveal the purpose of their stay).The amenities they offer (e.g., desks and Wi-Fi for professionals, cribs and baby gates for families).Evaluate Your Own SpaceYour property’s layout, amenities, and location may naturally cater to a specific audience.A cozy 1-bedroom apartment downtown might be ideal for professionals or couples.A 3-bedroom house with a yard might appeal more to families.Proximity to nightlife might cater to party groups.Experiment and AdjustIf you're unsure, start broad and monitor who books your property.

🌲🏕️ 🔹 114 acres of outdoor fun, developed in two phases:🔹 Phase 1 (60 acres) breaks ground in mid-2025, opening fall 2026🔹 Budget: $8.7M for design, permits & Phase 1 construction 🏞️ What to Expect in Phase 1:✅ 1-acre dog park (separate areas for big & small dogs) 🐕 ✅ Bike trails & nature-based playground 🚴‍♀️ ✅ Scenic rest areas, restrooms & picnic shelter🏕️ ✅ Multi-use path along Eastfield Rd + parking 🚗 📍 Location: 13729 Eastfield Rd, Huntersville, NC 28078 📊 Real Estate Snapshot (28269): 🏡 Avg Home Price: $384,732 (+5.1% YoY) 🏠 Avg.

Of course, track record and conservative vs. aggressive underwriting/promotion play a role in the reality of what you're hearing from any syndicator.