Underwriting your first Short term rental

[Sheldon Huff]

Hey BiggerPockets crew! I'm an active-duty pilot who bought my first deal a year ago (long-term rental) and now found a potential short-term rental in Pensacola's historic district. It's a $385,000 condo, 2-bed, 2.5-bath, 1,288 sq ft, using a VA loan (0% down). I've been digging into AirDNA and Airbnb listings nearby, and here's what I'm seeing:

• Slow Season (Nov-Feb): 45-55% occupancy (14-17 nights) at $225-$250/night = $3,150-$4,250 gross, ~$4,000 expenses (mortgage $2,485, taxes, cleaning, etc.). Net: -$889 to $250/month. Listings show 60%+ open days now (March-May), so I’m worried about vacancies.
• Busy Season (June-Aug): 75-85% occupancy (23-26 nights) at $275-$300/night = $6,325-$7,800 gross. Net: $1,819 to $3,100/month.
• Average: 60% (18 nights), $250/night = $286/month net, scaling to $1,500+ with upgrades ($275-$300, 70-75%).
  I've got $15k-$25k to invest (upgrades, buffer), but my reserves are tied up in crypto/stocks, which are down. I'm new to STRs and hesitant—scared it won't rent enough or managing it will be a nightmare after I PCS out of state in a year. I would live in it for the next year while renovating it to be ready for STR once I leave the area. Love the podcasts and have been listening for years, but am I over my head? Is this a great deal?
  Looking for military/STR pros to help me run the numbers or point me to a service for beginners to underwrite this. Is this worth the work, or should I pass? Thanks for any wisdom!