All Forum Posts by: Joe Whitley

I am not sure about Hawaii since I've never been there. However, as a STR for beachfront property, I would highly recommend a 3/3 unit. It offers greater flexibility for the number of guests the unit can hold. If children fit your demographic I would also recommend bunk beds in one of the rooms complete with games, tv, etc. I currently rent to up to 10 people however, most rentals don't include more than 4-5.

I deal with this issue all the time. It is extremely difficult to make a $$ provision for your time and expenses incurred when working on your property. I take a very conservative approach. My travel is measured by cost per mile used to travel to and from the property. Meals and related expenses should include receipts. Other expenses incurred that are required to fix up the property should also include receipts. Rule of thumb. All related expenses should be quantified and supported.Unfortunately, this should not include your invested time while working on the property that can be challenged by the IRS. Your CPA will know more about this issue. 

I own a rental house in Santa Rosa Beach, Florida. There continues to be a surge in last minute bookings over last year. In some cases guests are booking a week before their stay. Up about 8% over this time last year. The key is not to panic. We are gradually dropping prices and in some cases remain as one of the few houses remaining in the market.Margins and occupancy percentages are higher than last year do to stronger area demand.

Just keep a record of your purchases including intended use. Either method should work.

No question, rental real estate is the best investment provided you assess the risks and make it work for you. I’m in my 4th quarter and bought ocean front property 5 years ago. My family thought I was crazy. The property has since increased 82% in value, we use it frequently as a family for vacations and weekend get aways, greatly minimized my RMD requirement, break even each year on my taxes, etc. Now, who is the crazy one?

We currently own investment property in a residential community that has 84 homes. Like all other properties our home owners insurance continues to rise. One thought is to reach out to the HOA and negotiate a community wide package contract with a single vendor for Home owners insurance. This would be a basic package with available options offered to each participating home owner.. Any thoughts on the pros and cons of this approach?

Thank you

Great advice. One thing we have done was to offer amenities that carry high value in the area and build these costs into our rental agreement. For example, in the Destin area golf carts rent for 850-900 a week. We’ve negotiated with a rental company to provide the same six seater golf cart for 300 a week and it becomes part of the rental fee and contract. This gives us an opportunity to adjust the rental fee based on area demand. The guest sees the relative value and we are able to protect our margins.

What we are now experiencing in the short term rental market in post COVID hangover. This is not a bad thing for the ST market particularly if you have patience. We are experiencing a surge in last minute bookings. Unlike the past the guest audience in no longer planning their summer vacations months in advance. Instead they are looking for the last minute discounts. Therefore, if you are afraid you will miss the wave and drop your prices too early you will lose revenue potential. However, if you slowly adjust pricing in anticipation of a surge in demand you will experience greater returns. Just be patient. The Destin market was down 30 percent last year in short term rental income from the previous year. By following this practice I was up 3 percent from the previous year. You don’t need to fill your summer vacation calendar in April since the guest audience is no longer planning well in advance that is more characteristic of the pre Covid era.  Patience, patience, patience.