Side hustle?

I buy, maintain, and rent out houses - 3 long term rentals and one short term rental (near Disney). This year I made -$1,000 (not a typo). It was my best year yet!

In my younger days, I did security as an off duty officer, I taught the AAA safe driver course, and was a Disney Travel Agent.

I am saddened by my son commenting that his almost full time job (32 hrs/week) is exhausting. Where is the hustle? Between overtime and part time, I used to call my 60 hour week my short week.
Ouch,
‘so much risk!
what do you see as the reward?
 
DH and I are landlords for two separate vacation rental condos in the same high rise building in Ocean City, Maryland. A property management company handles everything.

Perhaps in 2025 we’ll stop renting out one and live in it full time from May to October.


Ocean City Police how may I help you?
Yes, I'd like to report someone for having a disser party and trashing my condo. Ok what's the name.
Onion boy
Click. Dial tone.
 

Ocean City Police how may I help you?
Yes, I'd like to report someone for having a disser party and trashing my condo. Ok what's the name.
Onion boy
Click. Dial tone.
All variations of your name are already on the “Do Not Rent To” list.
 
Ouch,
‘so much risk!
what do you see as the reward?
With the rentals? I budgeted for the risk. In other words, in a worst case scenario, I can cover losses for a wile. Hopefully, I will eventually have better luck with tenants and not have such a high turnover expense (I have one house that is a problem). As rents rise but my mortgages stays the same, I will eventually be at a point where I at least break even each year (and hopefully make a profit).

Rewards: If I do hold all the houses, my last mortgage will be paid off when I am 85 and my gross rental income (based on current prices) will be @$100K a year. But more realistically, I will one by one, sell houses and cash in on the equity.
 
/
With the rentals? I budgeted for the risk. In other words, in a worst case scenario, I can cover losses for a wile. Hopefully, I will eventually have better luck with tenants and not have such a high turnover expense (I have one house that is a problem). As rents rise but my mortgages stays the same, I will eventually be at a point where I at least break even each year (and hopefully make a profit).

Rewards: If I do hold all the houses, my last mortgage will be paid off when I am 85 and my gross rental income (based on current prices) will be @$100K a year. But more realistically, I will one by one, sell houses and cash in on the equity.
Ok,
So you’re doing the same thing with house that I did with my DVC points …
I get it now
 














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