All Forum Posts by: Will Quinn

Looking for some thoughts, on paying off a rental condo in Naples Florida.

The Background

I have a condo in Naples Florida 1 bed 1 bath. I bought it in 2022 for 180,000, and currently I owe 138,000 on the mortgage at 6.125% and escrow are insurance are 1103 a month. Hoa is 533 a month. I did a couple years renting it for high season and low season. Basically getting 1,000-3000 a year cashflow. Went over to a long term renter 1700 a month, great tenant so far past two years, cashflow almost even to 500 after minor repairs.

I have a second vacation home that I rent out 9 months and use for 3 months, the rent is pretty low for the off months so let’s say I spend 1000 a month to keep this property up after all expenses.

I have some cash and am running with the idea to pay off the Naples property to try and completely offset the vacation home. But I’m concerned with the market the property has lost value down to an estimate of 168,000 and hoas have gone up with insurance. Do I go find another property somewhere else to get my cashflow or just sink it in this property?

My wife an i are just closing on a property in Truckee, we intend to move into the property in ~2 years. In the meantime we plan to rent the property out. We have some experience renting property in Florida and Wisconsin but not in California. 

Understanding this is a very Tennent friendly state, does anyone have first hand good and or bad experiences in the area renting properties?

Specific Questions.

With a long term one year lease term, with month to month terms after, how difficult is the process to "force" the Tennent out if needed to move into the property as our primary residence.  

Ski Leases: Looking at the short term rental policies it does not cover leases longer than 30 days, seeing as there is a market for this type of rental what are peoples experience with this for ~4 month terms, and has it worked for summer leases as well.?

We are looking at purchasing a home and renting it out in an area that we want to live in eventually in the Tahoe area. We have a good apartment in socal in an area close to wife’s parents and looking to have children soon so want to stay close vs moving now. What are some of the considerations or pitfalls to this strategy where we would start renting a single family residence out, then convert to our primary residence after ~5 years. Looking at long term renting vs short term airbnb.