Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

90k liquid + 50k 401k loan + 35k sell company stock ...the other 30k to repair maybe HEL or LOC I made an error thinking i could borrow up to 50% of my 401k but found out it maxed 50k so now i have to sell the stock to make up the differences There other issue is the repayment of the 401k its has to be paid back to myself in 5 years. 

I think the problem might be that you asked the title agent that issued the policy and not somebody at the underwriter. 

I may need a real estate attorney for other issues as well.

Either way, grow/accumulate some more wealth just in case. 

The builder admitted they provided inaccurate information, and they proactively helped the home buyers affected by this issue to get exceptions allowing us to build a fence and plant shrubs on top of and beyond the easement line (but we still can't plant tress). hence, they refused to reimburse us furthermore. 

Some cities require the STR permit number in the title or very top of the OTA listing so city permit  technicians can scan and keep track otherwise the owner will be contacted and fined for forgetting or shut down if operating illegally.Some cities have a 24/7 STR hotline dedicated to receiving any complaints (from neighbors, HOA) for a code compliance officer to act onSome cities issue expensive fines for those operating without the STR permit

But agree that the condition of the roof could be an issue for your lender and your potential insurance carrier.

You will need to supply 2-3 quotes from different General Contractor's or licensed builder for all work.Some things that can occur are builder/vendor issues with lack of inventory, broken material, employee "no shows", date of completed work extensions, bad work, additional costs not factored on blue prints or cost analysis, delayed permits.Keep in mind any delays or issues will slow down your clear to close/funding date.

In Oregon (not just in Portland) you can't preemptively issue a no-cause eviction due to a property sale unless you have an accepted offer.If you are going to make an offer to the tenants to move out early or prior to your property going up for sale that offer can't be for less than what they would be eligible to automatically receive via Rental Relocation Assistance.