All Forum Posts by: Ian Tyndall

Hello! If you know all the investors then you could consider making a LLC partnership. The challenge will be liquidity. What do you do in 2 years if someone wants their money out?

I would shop the market and buy the property. You want to be in an area where the conditions are favorable, and then it all comes down to finding the right property to fit your buy box. 

You're on the right track, but keep in mind that STRs have the biggest impact on reducing Ordinary Income (W-2) taxes, not necessarily capital gains. Since long-term capital gains are already taxed at a lower rate (depending on your bracket), alternative strategies might be more effective for minimizing that burden.

1. STRs – Best for Reducing W-2 Income

If you prove material participation (500+ hours), STR losses from bonus depreciation & cost segregation can offset W-2 and other active income—a powerful tax strategy. Focus on high cash flow, stable regulation markets like:

Smoky Mountains, TN – High occupancy, low taxes

Florida Panhandle – No state income tax, strong demand

Arizona (Sedona/Scottsdale) – High ADRs, appreciation potential

Texas Hill Country – No state income tax, strong regional tourism

Use AirDNA or RABBU to validate your numbers, then move quickly—execution matters more than perfect market selection.

2. Alternatives for Capital Gains Reduction

Since capital gains are taxed lower than W-2 income, these strategies may offer better tax relief:

Opportunity Zones – Defer and reduce gains by reinvesting in Qualified Opportunity Funds.

Gifting Appreciated Stocks – Transfer to lower-income family members for potential 0% capital gains tax.

MLPs (Master Limited Partnerships) – Tax-advantaged investments that generate passive income with deferred tax liability.

Tax-Loss Harvesting – Sell underperforming assets to offset gains.

If reducing W-2 taxes is your priority, STRs are a great move. But if capital gains are the main concern, consider these other options. Pick a strategy and take action soon! Let me know if I can help.

Thanks. I was just adding this to my mental backlog of things to do before March 15!

This seemed like an unnecessary administrative complexity from the beginning. I get the original intent but it had the trappings of becoming a cottage industry like tax preparation. 

Hello! I have been studying it. There is a place near me that only does direct booking business and has amazing amenities: https://www.sandyriveroutdooradventures.com/luxury-tipis?srs...

I would probably go with something similar to host a luxury glamping experience with electric and running water/septic to encourage longer stays. Not sure if that would work, but I am actively looking at options. 

 Hello! AirDNA is great for gauging market demand. Avery’s method is great for competitive analysis. Both methods should be used together. AirDNA and PriceLabs both provide excellent data. If you configure your searches on AirDNA properly it can be extremely useful - remove listings below 4.7 stars, available > 220 days, etc. 

I have a place in Rockbridge Baths. I would be happy to take a look at what you are putting together and offer my opinion. Message me with your address and what customer segment / market you are going after and I will offer up my thoughts. Best of luck!

Throw pillows…

Fake plants…

These are needed to spruce up bedrooms, bathrooms and outdoor spaces. How to match them and where to get them?

Kenzer, 

To your first question about liability, yes a LLC can help protect your assets from taken, but you have to manage it correctly. I recommend that you contact a lawyer to setup this process for you. You will want to transfer the deed for the home to the LLC. You might even want to setup a C-Corp (for tax and liability reasons as well) to manage the business with the guests and pay rent to your LLC. This is a bit more involved, but as you scale, it is something you should consider.

In response to your second question, I would say "yes" to allowing pets. They are coming to your property if you allow them or not (you cannot forbid service animals) 
Consider the facts: https://www.dogster.com/statistics/pet-travel-statistics-tre....

Top 12 Pet Travel Statistics
78% of American pet owners travel with their pets each year.
54% of cat and dog owners plan to travel with their pet.
58% of people would prefer to travel with their pet over a friend or family member.
52% of travelers base their travel plans on accommodating pets.
About 75% of luxury, mid-scale, and economy hotels allow pets.
In 2019, a total of 404,556 animals were transported by airline.
Nearly 64% of travelers prefer to travel with pets by car.
42.9% of people look for a destination with hiking and fresh air for pet travel.
Dogs make up 58% of the pets traveling around the world.
37% of owners take shorter vacations because of their pets.
10% of travelers have hidden their dogs to travel.
27% of dog owners go the extra mile for their pets.