In my experience, a property with multiple cottages and outbuildings can provide all kinds of creative strategies...some folks try short-term rentals or even specialized retreats if local regulations allow.

What areas do you specialize in?

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

I specialize in STR/MTR and I have managed a few in Oceanside.

Hi Monish, my partner and I specialize in STR investing in AZ.

The seller had a military contractor job with security clearance.

If there was no appreciation, there is no need to do a 1031 exchange.I have never been a fan of condo's as you lose some control over the investment - You have no control over the monthly maintenance fees, you may not have control over who is on the board, you have no control over special assessments.I wish the investments turn out well for you!

You should have a good idea of every expense you have in your primary home, then add the STR specific:  (These are rough estimate numbers, depending on various factors)STR insurance - a special insurance that covers both the property and your liability, could be $2~4k in areas without natural disasters, could be more than $10k in some other areas.cleaning fee - approx. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

I specialize In helping investors like yourself locate, and secure investment properties and provide a hands off experience along the way.

@Kyle CarterFor PM, ask how many rental properties they currently manage, what types of properties they specialize in, and their process for screening tenants and handling maintenance issues.