If we're going to just talk in hypotheticals, of course anything is probably possible anywhere but highly unlikely. 

Some of the materials we choose and asked him to pick up (such as flooring) he replaced with low quality materials, I assume to keep more of our money for himself. 

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

@Gash Nookala,Renting can indeed be slower in winter, but here are some tips to boost interest:Enhance Listing: Ensure your listing has detailed descriptions and high-quality photos—consider professional photography if needed.Competitive Pricing: Double-check local comps; even a slight price adjustment or incentives (like a reduced deposit) could attract more interest.Broaden Marketing: Beyond Zillow, Hemlane, and MLS, use social media, community boards, and local business connections to reach a wider audience.Flexible Lease Terms: Offering shorter or month-to-month leases might appeal to tenants during this slower season.Local Property Manager: A local pro can tap into their network and help fill the vacancy faster.These steps should help you find a tenant despite the seasonal slowdown.

The FF rates in my zipcode are higher than I expected and their quality is less than what I'm bringing online! 

.• Use some equity from the sale to make this transition smoother.I’m torn between maintaining our current home as an asset and buying  a new smaller house to use as a rental after we move back in versus simplifying and focusing on a single upgraded property Considering factors like market trends, potential equity growth, and quality of life, which path do you think would be most beneficial?

If the owner redeems the 2nd month after you bought the OTC, you only get the 3% (1.5% x 2 months).Exercise those due diligence skills!

It depends on your financial strength, the quality of the property, how many properties you own, etc.I like to start with one significant expense and three months of vacancy.

Lei, I'd be happy to serve you any way I can.For Ko'olina, I love the Beach Villas (as well as the entire Ko'olina area) and if you are primarily looking for a very quality property for you and your family to use, I'd recommend it.  

I would only do this if you can find a quality property manager.