It is currently a glorified finished attic with little room- Use addition and raise it up and extend it to the side of the home for more finished space and room for deck, washer/dryer room etc- Make the living space as functional as possible with the added sqft- Add outside living structures like deckThis is a fairly wealthily area and I want to maximize my ROIWhat are some things you recommend for a large scale project like this and what are some hurdles ?

When one of my top contractors and I just started working together and we hadn't built up our current level of trust, we structured our first deal like this:-I purchased all supplies.

I understand each comapny structure and risk and I do respect it. 

The only difference is the structure? 

Sometimes pulling out equity and reinvesting it elsewhere..maybe in a smaller, more agile asset..can give you the cash flow boost you’re after without giving up a solid property.Improving the property’s current performance by making it more appealing to tenants or tweaking lease structures could give you a nice bump.

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

Whether they’re navigating their first deal, figuring out how to structure financing, or learning the value of patience, my clients gain confidence knowing they have someone who’s been there.

Definitely get the structural engineer to look at the joists & support beams to see what's up with the uneven floors.

Assess Your Goals and Current Structure: Beyond replacing your handyman team, it’s important to evaluate your portfolio’s current management framework and clarify your long-term objectives.How are responsibilities currently divided among you and any co-owners or family members?

To anyone considering such generational structure, I suggest: - Wyoming as a organization state.