There are just too many variables to consider.So, just make sure your calls are short and sweet: Get the high-level facts and then wrap it up!

He is definitely a person/business that we are trying to model in the general contracting space here in Chicago. 

We are also in the CRE space, so I'd be happy to offer any advice I can.

Plus more wear-and-tear on the house and more cleaning to do (and pay for).I prefer @Bradley Buxton s idea of adding more amenities instead.

I totally agree and had he listed 'prepping caulking and taping house exterior' as a separate 'project' and 'painting house exterior' each with its own separate respective labor quote, I would then consider.However since he and I have discussed the CSLB limit time and time again, yet he still had the nerve to just simply list (on a spreadsheet) $500 labor for painting the house alone, and handed me the sheet with a statement that my compensation is not 'fair', the long and short of it is this person who I consider a friend, isn't any longer a viable handyman for law is law, business is business, and fair is fair.Note: had he quoted something like $400 or something for painting house, I would be glad to negotiate with him (ie, maybe he was under the misunderstanding that $100 would be enough for paint) but he didnt. 

I've heard the Short-Term Mortgage Shop can help with that.

Now, I have a portfolio of Short Term Rentals and Long Term Rentals.I've also helped other investors with their DSCR loans and flip projects.

We are transitioning into the US Market particularly Texas.

This is a very different model than the owning your own asset and managing yourself to optimize cash flow like in Short Term Rental Long Term Wealth, but it is a legit syndication.I have not personally invested with them but I know their head of data very well and I have seen that their underwriting is RIGOROUS.

In Colorado we are capped at 2 month's deposit.