At settlement what is sold is the beneficial interest in the trust rather than the property itself.On paper the lender just sees a common estate planning tactic rather than a sale of the property.

I look forward to learning as I go, but I'd also love to hear your advice and common mistakes to avoid.

Common concerns in pre-1940s buildings include outdated plumbing, old electrical systems, and structural issues that could be costly to bring up to modern standards.

In terms of my background, we have four properties all in the same vacation rental market and we most commonly book through VRBO.

This comes with time and experience but a book that helped me tremendously (not really a sales book, though) was "Boundaries" by Henry Cloud.The most common challenges for RE Agents early relate to generating leads and focusing on income producing activity.I would consider spending 50-75% of your side-hustle time on income generating activities. 

While some may prefer a single treatment, opting for an annual plan with quarterly visits often pays off, especially if termites are common in your area.

More often, I see people in Chicago using the MTR strategy to side step the STR regulations.I've considered buying a SFH with an in-law arrangement in Chicago to use as an STR because to me that seems like the best way to employ the strategy.

First, yes, this is a very common form of agent marketing. 

Thanks in advance,DavidDavidThe home equity line of credit can be assumed -- it is cancelled with the bank at closing so no further funds can be obtained.It is common and same as assuming a non-heloc mortgage.Alan

That will be pretty common with a lot of suburbs on the east side.