There’s also the free advice from Rabbu that’s great.

Go to meetups, offer to help people FOR FREE, ask for book recommendations, read the books and follow up with the people who recommended them. 

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".

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

@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 

If you need to talk through this in more detail feel free to reach out.

Download the free Deal Check app and start playing around with numbers and figure out how to analyze a deal.

Don’t be free and loose with your friend’s money. 

Feel free to reach out, happy to chat further. 

Feel free to DM me some initial details, didn’t see any on the website. :)