If the deal makes sense I think the pros will outweigh the cons.

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value. 

It kills 2 birds with 1 stone in the sense that it offers me evidence that the property is cleaned and everything is in place before guests arrive and watching video after guest departs helps me make sure everything is there, and nothing is missing / damaged from last group.

I spent the last two weeks down there house hunting but didn't see a deal that made sense in my model, but would love to connect with another Jax investor. 

However, we also recognize the time value of money, so while it might pencil out to turn a profit, but we get an immediate payback versus a six to nine month holding time, it might make more sense to sell them both as bare land.  

Quote from @Marshall Robins: Quote from @Felicia Richardson: Ahhh, that makes sense.

Meetups, conferences, social media - connecting with as many people as makes sense and just discussing investing and what you do and if you found X would they be interested in investing with you.

A savy agent sensing a situation like that might simply ask for proof of funds before showing the house which a nosey neighbor is unlikely to have.

I'm more so wondering what makes the most sense as I do want to treat my investing journey as a business.Thank you in advance for your advice!  

This makes more sense to me now, too.