All Forum Posts by: Stefanie K.
Stefanie K. has started 6 posts and replied 45 times.
Post: Tax Free Gains for Primary Residence (2 of 5 moving to 5 of 8)

- Investor
- Chicago, IL
- Posts 50
- Votes 13
@Jay Helms Yes, but why would I opt for a 1031 if I can take the gains tax free today? The value of this Primary Residence rule is that there is so much more flexibility with simply getting all the gains. I can then choose how much I want to leverage again to buy another property or diversify my investment portfolio with another portion of the gains.
Post: Tax Free Gains for Primary Residence (2 of 5 moving to 5 of 8)

- Investor
- Chicago, IL
- Posts 50
- Votes 13
Great to confirm! In either case...curious what folks consider when deciding whether to sell to take tax free gains. Luckily, we fit either model since we did live there for 5 years before moving...
Post: Auto shutoff toilet valves - has anyone used one?

- Investor
- Chicago, IL
- Posts 50
- Votes 13
I try to prevent problems before they arise. When I buy a property, I check the toilet guts and if they appear to be old, I simply replace them. $15/20 minute job will buy you several years of never even worrying about this. I haven't had a new one "go bad" so I don't know the average life span...once I know that, I will just plan on replace the guts every X years proactively
Post: Lease property to AirBnB professional?

- Investor
- Chicago, IL
- Posts 50
- Votes 13
I own LTR and also do Airbnb. If you don't want to do Airbnb yourself (it is work...far less passive than LTR), I think renting to a pro would be fine BUT I would ask for (1) higher rent...some % higher 15%-20% over market rate (2) ask for profit share (some % of gross rent). That way, all incentives are aligned to make it a great experience for you and guests.
Win-Win...you take the real estate risk, they get more units, you each share in the upside of a higher revenue lease model.
Post: Outsourcing Landlord Duties Without PM

- Investor
- Chicago, IL
- Posts 50
- Votes 13
+1 to Cozy. I use it for all my LTR and it's so simple. Tenants love it to. My tenants tend to be younger and very open to technology and automating monthly bills. Also, it's F.R.E.E...
Post: Tax Free Gains for Primary Residence (2 of 5 moving to 5 of 8)

- Investor
- Chicago, IL
- Posts 50
- Votes 13
Hi BP - Curious what others have done when faced with the deadline to sell under the current "2 of 5 year" rule and soon to be "5 of 8 year" rule in order to take gains tax free on a primary residence.
We own a very nice condo in Chicago in a very good neighborhood. We bought at the bottom and the market has since gone a little crazy in Chicago and we now have a lot of equity should we choose to sell. We use the condo for Airbnb (moved into a multi unit 1 year ago to make that our primary residence) and make solid cash flow on it. We are mostly buy and hold investors and buy for cashflow.
We do think there is extreme value in selling while we still meet the "5 of 8" criteria under the new proposed tax legislation. Taking our gains tax free and then holding for another great opportunity to buy. Anyone else thinking about this and what are some of the other factors impacting your decision? I am leaning heavily towards selling and locking in those gains tax free...thoughts?
Post: Mistakes when starting out

- Investor
- Chicago, IL
- Posts 50
- Votes 13
Figure out how to not waste your valuable time: Look at enough deals "on paper" (usually online) to know if it's even worth walking into a property. If I am SEEING a property, I already have a general sense of a price where it's worth it, I am just visiting to see general condition, immediate neighborhood, etc. By the time I walk out the door, I will be able to make a decision by EOD with either an offer or not. I've heard of people visiting over 100 places before they buy 1 (this seems CCRRRAAZZZY to me!). In my opinion, these kinda people either have no idea what they want, unrealistic expectations about price, or just REALLY like to window shop. I haven't looked at even a fraction of that many places in persona and I have a nice little highly cash flowing portfolio going. Know your numbers, know your risk tolerance, don't fall into the analysis paralysis trap and be ready to execute when you find something that works!
Post: Best automated message service you've found

- Investor
- Chicago, IL
- Posts 50
- Votes 13
Hey @Jon Crosby No, I wouldn't want to respond to bad guests but that's <1% of all the reviews I give. I would, ideally, like to be able to select either the good or bad guests and from a list (tick boxes?) and once the stay has concluded, have the service push out some canned responses. It sounds like Smartbnb may have this capability already baked into the platform but I have not seen it fully in action.
Prospective guests don't see the reviews I give guests, only the ones guests leave for me so there is really no "I am not providing personal review" risk. I do a version this today, albiet it's rather manual. I have a list of generic, "GOOD" review templates and I just copy and paste them into the review section of Airbnb. This model has never hindered me or made it seem automated. I would just like the ability for that to happen seamlessly without me needing to go in and click all the button for each review.
Post: Best automated message service you've found

- Investor
- Chicago, IL
- Posts 50
- Votes 13
Nope :) For one, reviews cannot be done with templates . You can save templates, but you still need to log in, select the one you want, and send. I am looking for something a touch more automated than that...
Post: Looking Ahead - What can I do TODAY to prepare for no W2

- Investor
- Chicago, IL
- Posts 50
- Votes 13
@Shawn Ward Thanks Shawn. I have/will be replacing some W2 with rental income (4 STR, 2 LTR currently) and my spouse will continue to be self employed. Wholesaling just isn't my game. I have a buy and hold strategy while leveraging STR for great cash flow and coc returns.