All Forum Posts by: Jake Gove

We are in the process of getting ready to close on an investment house we will rent out as a short term rental. I was planning to create an LLC for the investment and use it for all expenses and income related to the rental. I read that the new tax bill affects deductions. Will I no longer be able to deduct expenses for the investment unless they end up being higher than the 24k standard deduction for a married couple or will I be able to take the 24k deduction for ourselves and still deduct investment expenses because of the LLC?

I have a house in Winter Garden that I am considering using as a short term rental, but I had heard that they are not allowed in Orange County.  However, I saw this: http://www.orlandosentinel.com/business/os-orange-county-airbnb-20160520-story.html  which indicates that Airbnb is OK?   Can someone please let me know what the situation is in Orange County?

My rental has been vacant for the last three months, so we have put it up for sale and have had very little interest.  I think it's due to the size.  It's a 4500 sq ft house that had been rented out for the last five years.  The renter left and we can't go lower on the rent or we will not even break even with the mortgage and all the fees (landscaping, pest, property mgmt, etc.).   We were considering rented it out via VRBO or AirBnB but that would require either furniture rental or a big furniture purchase, again killing any profits we could make.  Also, since it's in Orange County, I've heard VRBO and AirBnB are not a good idea.

I would also be interested.   I have a SF property in Winter Garden I just listed and once it sells want to do a 1031 exchange for MF (not in war zone).  I thought near Disney would be an issue because of Orange County prohibiting short term rentals? Can you explain?

Any opinions on Leesburg?  I live in Colorado but I have a SF home I am going to sell in Winter Garden and I'm thinking about MF properties.   A guy on Facebook mentioned he had a MF property in Leesburg for sale.

We built the house in 2011, and lived in it until July 2012. Then we rented it out until this summer to a single renter. We were making a few hundred a month after everything. We haven't been able to find a renter since. Our property management company has been trying to market it and it's costing us a lot each month with the mortgage, the landscaping, the pest control, the property management fees, the HOA, etc. We also had to pay a lot to get it painted after the renter moved out. From making a few hundred extra a month to having to pull thousands from savings to maintain it this summer. That's why it looks like we have to sell. I just think it's too big to find a renter and have them pay what we need to make a profit. We had hoped to hold onto to it.

Thanks for the info, Bill and Dave.   Having never done a 1031, that's good news to me.  I would love to get into MF to increase monthly cashflow.  The problem is I'm not sure where to buy.

There was a smaller townhouse one in the community, but it was listed as 30 day rental only.   I don't think I'd be likely to find many 30 day rentals for my property and it would cost me too much to keep it.

Thanks for the responses.  Looks like my only option would be to sell it.  My first preference would have been to keep it and rent it but I can't find renters and it's costing me a lot of money to hold on to it.   I have heard about 1031 exchange and if I sell it would love to pick up a couple of condos (i.e., something smaller that would be easier to rent).   Is the condo market around Orlando viable?

I own a 4500 sq ft 5 bedroom, 4 bathroom house in Winter Garden that I have been renting out since 2012. The renter moved out and I have been unable to find a new renter for a price where I can break even. It is very close to Disney World, so at first I was excited that I could luxury furnish it (it has two other rooms that could be bedrooms so 7 total) and rent it out to large families via AirBnb or VRBO/HomeAway and occasionally use it myself with my own friends/family. I was encouraged by $300 a night rates I was seeing on AirBnb for a home of this size. Then I found out the HOA does not allow short term rentals. Do I rent furnishings and go for it on AirBnb or just sell it? What do HOAs do when they find out? I live in another state so I need to have a property management company handle it for me. Any advice?