@DemarquisMaybe initially see  if you can do a Joint Venture with an experienced investor to get feet wet

Joint ventures on STR or on flips would help you scale 

If for example there were signs of root infiltration through a joint or something, I would consider taking an action, BUT that might not mean replacing the line. 

We jointly took part in the design phase, and they got what they wanted and I got what I wanted.

Partnering with investors  and also doing flips using a Joint Venture would get you  more capital!!

I have 2 separate Property owners where im located in Maine both looking to do joint venture deals where they provide the land and I get the project lined up and funded.

Depending on what the line looks like (i.e. if it's just a small gap in a joint/imperfection in the line that the roots are growing in, and not that a whole section of the line has collapsed or anything like that) then you can probably try this first before replacing the line.

are they filing tax returns jointly or "married filing separately"?

Most leases make tenants like this "jointly and severally liable" meaning they are BOTH responsible.

Thus, as I am at this point a ‘hobbyist’ and not a professional I presumed I would simply report whatever minimal profit or loss realized on this first joint flip project as pass through income.