The major concerns where I feel we have leverage are 1) the roof needs replacing-there is wind damage 2) there is a slope towards the house which needs correcting (we think this can be fixed with a French drain) and 3) there is a giant tree right by the house with roots visible to the slab. 

Wow those giant luxury buildings, and possably changing 2 yr to 3 yr, are big time game changers for the inventory of 100 year old duplexes.

If it was me, to start i would try to rent out the extra rooms. maybe consider using ABnB to get your feet wet. if you want something long term then look at TransUnion smartmove for your background checks. see if you can find a landlord near you that'll give you a lease agreement, but look into some real legal counsel. also... i HATE HOAs. if your not a dick and you take the time to make the space look better, if renting is not liked they might let it slide... but check the rules, they might not have anything against it  

Find a small/mid sized mortgage company rather than the big buys that for the most part are giant call centers. 

New Large Skylight and Slider that goes to Deck, Giant Cedar Closet and Immense Bathroom that has a soaking, tub double vanity and Sauna.

After cosmetic work to upgrade the interior and furnish, building a social media presence, and adding a GIANT hot tub, Success!

Just a giant game of wack-a-mole.   

Some have found deals, others have found it to be a giant waste of time.

He has thrown me into a GIANT MESS!

I landed a job as a supply chain manager and after a year I left to be a Chemist for a large generics pharmaceutical giant.