Today it will be very challenging as the rates on HELOC’s will be very high.Unless you perform the labor or get a screaming deal, your chances of getting all your money out will be challenging and it may end up being near 100% financing and thus little to no cash flowNot saying it cannot be done but in high interest rate environment brrr makes it that much harder

Could be the just todays market environment.

In this environment I wouldn't put all my eggs in the STR basket.If your insentent on this then you must put a lot of effort into vetting the area, the rules, the property etc to make absolutely sure a given property will cashflow with conservative numbers and what your exit strategy per property is if they don't go as anticipated.

For stocks, in this environment, I would only own large cap companies with a solid history of increasing dividends year after year, and reinvest the dividends which decreases your cost basis over time.

But it’s been really great having them in this environment/ touching on the investment life education (ex; we live upstairs ..’shh no jumping and running..it’s late and we have tenants’) / starting our family here. 

In a volatile interest rate environment the cap rates have significant lag time in reflecting the interest rate at which the property can secure.

Are there any resources here that can help me create an investor-friendly agent environment so I'm not turning away investors due to misunderstandings on both our parts?

Optimized doesn't just mean your digital environment, but all the basics like making sure the rooms look photogenic and have an Instagrammable moment, having backups off all bedding and replaceable items so your property always looks like the pictures, setting up strategic partnerships with local businesses, tour guides, etc...As far as management - make sure to have a handful of cleaners and contractors on good terms. 

It was too easy to make money in STRs and MTRs over the last several years but as we return to a more normal environment that's no longer the case.

So my question is, considering the environment and my situation, how should I determine whether a property would be a decent deal?