What sort of market research did you do prior to investing in OH specifically when trying to capture the insurance market?

Finally, look into house hacking as this is a really great way to gain sweat equity in a property that can be captured in a tax advantaged way every couple of years. 

This further supports my concern that I overpriced our summer months and thus had to significantly reduce rates to capture summer reservations. 

@Ian Hoover I believe that craigslist has been making a lot of changes over the past 6 months, most of which are to discourage the use of things like postlet ads and spam.Here are their rules:Lead capture, loans/financing, services, offers to buy, lists/directories, and/or driving users to a website are not allowed.please do include:all relevant information about the specific property you are sellingmultiple high-quality photographs of the specific property on offerstreet address, and location on craigslist mapplease do NOT include:cartoon or graphic images, photographs of yourself or other peoplelinks to "more information" elsewherephotos with "click below," contact info, or other writingsearch links, or information about multiple propertiesadvertisement for services of any kind, including financing or loan informationadvice about buying and/or selling and/or market conditionsSo the basically made it so that you can't have links on your posts, and your posts have to only be for one piece of property, and all the information has to be contained in the ad.

Your words are captured forever and ever and ever.  

Lastly, I often times have completed 1031 exchanges when I want to sell to capture equity and trade into a larger property. 

Use Open Home Pro or similar to capture leads.- Run broker's open house (if those are done in your area), with a lender attending.  

Landing pages for lead capture, Local search engine traffic for the website, email campaigns with a keen ability to focus and find specific information in a very short amount of time.

A year later, do a cash out refi, capturing your sweat equity, and put that money down on the next. 

I think this captures the situation quite well.