I am seeing a large increase in demand for STRs here and am contemplating developing solely for the purpose of creating a perfect STR.  

We own another single family home that we are contemplating selling to recoup the equity required for the 25% down if all else fails, however, we'd love to keep it if we can find another lending opportunity.

Just get your license and operate within the law.PS - here's a question to contemplate if you're going to be honest with yourself. 

The receiver can read and contemplate the initial reach in their own time and it's less disrupting. 

However, if you think of leveraging the cash value as a "double play", then what you are contemplating doing is a triple play: using borrowed money to fund the life insurance policy that will in turn fund the real estate investments. you would be literally putting your money to working three places at one time.However, most life insurance companies will not take your premium if they know the source of funds is a home equity loan.The concept of leveraging a high cash value life insurance policy to invest in real estate is thoroughly discussed in this thread...https://www.biggerpockets.com/...If you assume the use of a HELOC on the front end of all this, it all gets done with borrowed money...

I renovated a house recently and I’m contemplating rather I should list it and sell it myself or hire a realtor at my office and just get a finders fee.

I will contemplate your questions further and take it into account moving forward.

if my client or myself was in a similar situation my advice to myself and my client would be... if the situation is truly calling for you and your family to be in a better living situation and if you have the capital to purchase a townhome and it doesn't put your financial family in a financial stress, instead, if it provides you with the opportunity to reducing your living cost and gain equity as well and provides you and your family with the comfort you need, then it may definitley be a choice you may need to investigate and contemplate a bit more... but if you can hold out a bit longer and find that deal that could provide you with the ideal set up with a 2 family home and renting out the other side etc, the only positive about this situation is you may have a similar set up in terms of finance compared to the townhome but you might be gaining a bit more equity without you putting your hard earned money into it due to the tenant paying a portion of the mortgage...It's definitley something to consider, and take into consideration theres news mentioning rate cuts for 2024, which it might be able to provide you with better profit margins for an investment or an even a lower mortg payment for you townhome!

I have been contemplating building multis as well, i figure self GC'ing i should be able to build for around $75K/unit without a basement, and Me being the HVAC, finish, cabinet, flooring ect guy. 

I understand we can always plan and schedule better , but wanted to understand if you have identified any money saving opportunitiesThe main home is used as a short term rental, so I was actually contemplating today if it would have been better to plan a 1-2 month vacancy where the power could be shut off instead of needing the temporary power pole when factoring in the labor and materials, city permit fees and utility fees.