People drive 10 to 15 minutes more, and have a better experience.Also there are traffic and parking requirements.

This is why you have the annual reporting requirement when you have 1031'd out of state.  

When I speak to finance institutions, I am only offered non-conventional loans for investment properties which require high down payments and significantly higher interest rates.

If anyone has insights on how to get started with licensing in Illinois or advice on balancing it with investing, I’d greatly appreciate your guidance!

Our engineering team finishes in roughly 2-3 weeks with no major modifications required to our initial architectural plan.

When you say the older vintage properties cash flow better I’m concerned you’re focusing in on properties  in areas that are below today’s replacement cost but in areas that cannot absorb the required capex.

Is it a must to have a property manager on the vacation rental due to the city rental database requirement?

Hi Dustin, All bridge and HMLs require an LLC as they are business purpose financing products.

Gradually transition to larger, higher-end projects as you gain confidence and expertise, balancing risk and reward.

Pretty solid points here, I would also like to add refinancing with a non-traditional DSCR based loan can assist with getting access to cash quickly as there are many lenders that have a lower seasoning requirement.