All Forum Posts by: Craig Lillard
Craig Lillard has started 1 posts and replied 5 times.
Post: Serial vacation rental strategy. How does this sound?

- Posts 5
- Votes 4
@Austin Brewer
Yeah that makes sense Austin. Good idea. Thanks for posting.
Post: Serial vacation rental strategy. How does this sound?

- Posts 5
- Votes 4
@Hailey Lanier. Sounds good Hailey! PM me anytime.
Post: Serial vacation rental strategy. How does this sound?

- Posts 5
- Votes 4
@Collin Chan. Lol! Funny you mention that. I was totally thinking about the house swamping thing a couple of days ago. I’m not sure how it would work from an investment standpoint. I haven’t looked but I’m sure there’s a platform out there for this. But, I am tracking with you for sure.
And I have thought about the things you mentioned, i.e. long-distance investing and the problems that could go along with that.
I do think that living there first and being able to get a lay of the land and make connections with quality people could make that easier but I’m sure it’s not the ideal from an investment standpoint.
I also considered purchasing a reasonably priced RV that could be used to go from place to place and as a back up residence when needed.
I don’t think I am considering doing this worldwide. I thought about it but I think that definitely adds a bit of complexity that I’m not sure I would want to deal with. Probably Hawaii is as far as I would go, But then again I still need to research areas and where the best bang for your buck is.. I guess if everything lined up I would consider it.
- Craig
Post: Serial vacation rental strategy. How does this sound?

- Posts 5
- Votes 4
Thanks everyone for the responses! Let me post a general thanks here and then will comment directly as I am able. I really appreciate it all the feedback. I am at the very beginning of this and wouldn't be pulling any triggers for 1 to 2 years anyway, so I don't see any harm in starting to consider the concept COVID or no COVID. And as I mentioned, I would live in the first one and not move out until I am sure I can move. The other alternative would be to do long-term rentals instead and not move out of each place ONLY once I have a long-term tenant moved in.
I have been an internet entrenrepeneur for 20 yrs or so now, and am looking for diversity. However, I have been through my own business ups and downs and not ignorant to losing big. This is one of the reasons I am looking to real estate for some diversity.
Locally, I have been watching rental properties in my area not moving for the last 6-8 months, so this is definitely on my radar.
So, I am at the very beginning of this journey, and just wondering if, apart from COVID, this is a crazy idea or not. Sounds like it's definitely something to look into further.
Thanks again!
:)
- Craig
Post: Serial vacation rental strategy. How does this sound?

- Posts 5
- Votes 4
Hi! New member here. My wife and I are ready to go see the world a bit and I have pondered this strategy. Would love some feedback. What I was thinking we might do is choose an area of the country we want to spend some time in. Go there and buy a vacation property. Possibly one that could use some work.
Stay as long as we want and fix it up and when ready, start renting it out as a vacation property and move somewhere else and repeat. Would have to find a property manager of some sort to manage it.
So, in 4-5 years we would build up a small portfolio of properties in places we like and would like to return to.
My current business would allow me the ability to do this, so there isn’t anything holding me back from that perspective. Just wondering if there is some flaw in my plan I’m not considering.
Thanks!