Feel free to reach out if any questions arise.

They typically have a "designer" or "consultant" for free that can give advice (or research in your case) specific items.

Many companies I found do not want to cover a lot of homes because of the items you stated but with that the hurricanes and also in florida many roofing companies have done the "I will replace your roof for free, just let me deal with the insurance company".

I also do Short term rentals which I feel only a small people do it right in this area and which is why I chose that market. 

Feel free to reach out.

If you have any questions or opportunities you'd like to discuss, please feel free to reach out.Thank you for welcoming me to the forum!

Feel free to reach out if you have any questions!

@Samuel Metcalf- thanks   1) I would recomend getting a HELOC in place on your primary residence duplex  for  as much as  possible...this should be available for  free or a low  cost and the rate will be variable in the  8-11%  range ...prime rate +  margin of  1-3% ) ...the min payment is in interest only payment on outstanding balance   2)  use the heloc for the  remodeling  costs ...pay it down as  agressively as you can   3) on the  purchase of the investmenet  1 unit -  you are  allowed to put as little as 15%  of the price for your down payment ...the pricing you get for the loan will improve  as your down payment  grows so you might look at  75% /  80%  and  85%  ltv  options 

BRRRR is a great option here and tons of price points.I like @Jonathan Greene Q - Do you want to move to Chicago are you feeling like you have to? 

Feel free to share: better-informed agents and LOs provide more valuable counsel to their Investor clients!