All Forum Posts by: Sean O'Keefe

 Hi Sean, 

With all due respect, unlikely meeting the requirements is not very useful information. This leaves a lot of room for interpretation and that is exactly the issue we are having at the moment. So far it sounds like we will just need to verify via a CPA, which is fine, if that is what we need to do.  I was hoping some folks might be in a similar situation or had a similar experience and might be able to share. I do appreciate you taking the time to respond regardless.

My husband and I are ready to invest in our first vacation property, likely in Florida. We hope to eventually have multiple properties, but want to take our time to learn and make the right decisions with our first rental. I should add it will be a short term rental property. 

What adds complexity to our plan, is that we live in Minnesota. We would like for the investment to be treated as active, of course. However, we will likely need a property manager to assist with some facets of running this rental (since we would not live locally) and would primarily market it through platforms such as Airbnb and VRBO to start, (eventually setting up a direct booking process).

Here's our question for those who have experience in STR's or who might be involved in a similar scenario: How challenging is it to meet the material participation hours needed to achieve active status? My husband is a high income W2 earner, and meeting active criteria would put some of our tax dollars back in our pocket. Is it possible to have a property manager who manages some of the property, while I manage the rest remotely? For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest? (i.e. initial decorating and painting, bookings, rate structures, marketing, bookkeeping housekeeping, etc)?

According to what I have read straight from the IRS website and other places, we need to either meet 500 hours, or at least 100 hours and also work more than anyone else on the property. I feel I could definitely meet both of those on my own, as my husband works full-time , and I will be the only person besides the hourly employees stated above that would be accruing hours. However, the one CPA I briefly talked to said the investment would be treated as passive. No real explanation as to why or whether there were exceptions to that. 

We are newbies, and don't want to miss out on a great investment and tax savings opportunity, but obviously want to do everything correctly in the eyes of Uncle Sam. Thank you so much in advance for your help.

I’m doing medium term rentals and I’m breaking even cash flow wise. Some months I’ve unfortunately had to pay like $150 out of pocket but I’m Planning on holding long term wise and the let the rental bare fruit later in my life because I’m only 22 and just wanted a base hit or a rental in a great neighborhood. I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season 

 Thanks for that clarification.  I've heard at least some of this before, but I'm paranoid and don't necessarily take the best notes of what I bought etc, so the physical receipt is a nice tangible record if I ever need to justify an expense.  And in most cases, reading a receipt and knowing which property/my management company it is tied to (done automatically by separate accounts linking to my software), even if I don't do a very good job documenting, I have enough to go back and justify almost any expense.  

I want simple - quick picture as soon as I leave the store, so I don't have to track expenses.  I need to experiment with the RH option... it takes a few clicks to get to the option, but supposedly it will try to reconcile the bank pulled transactions and receipts for me, so if it does do that, would be nice.

This is an old thread, but curious if many of you who started RentalHero (RH) back then are still using it?  I've been using it a few years as well and mostly like it for my smaller portfolio across multiple entities and states.  

The thing I'm trying to do better with going into the new year is handling receipts.  I have never used that feature in RH, are any of you using that?  I'm thinking that I need to go to an electronic receipt tracking system, I've been doing it old school all these years - dump them on my desk, some month down the road go through them all and file them to folders for reach property, start a new folder each year.  Not bad, but a lot of work and hard to find a specific expense if I can't remember it when I'm categorizing the expense a week later in RH or something.  

Anyway, what are you guys that use RH doing for receipt tracking?  

Guys - I am a limited partner & invest in a multi-family building passively that was sold resulting in passive gains for 2024. There are some accumulated passive losses but not much. Can I sell some of my stock held long-term for 3 yrs at etrade to further offset the gains? Thanks

Not a silly question at all but the answer depends on a few factors. If I assume this is a rental property, your income isn't over $150k, and you're not a real estate professional then the losses the rental property generates could offset other income up to a certain amount. 

This means you'll want to "write off" expenses related to a property you have in service because if those expenses don't benefit you this year they could in the future once you sell the property.

We can get into a lot more details with the "if" "and" or "buts" BUT I think this would be the "simplest" answer without diving into your specific situation here.

I hope this helps!
 

We have 3 rentals in CA and one in Kentucky (total value about 2.5 M)

some W2 income

some pension income

some syndication income and some from a business (s corp) 

Are there any issues/problems If I want to purchase a rental property in Pennsylvania with my New York York LLC? If so, are there any steps I need to take that would allow this to happen?