However, I toy with the idea of leveraging our properties to find the next investment that could bring in the income to bring my wife home from work or at least give her the OPTION.

Daughter hauled *** and they're no longer talking.

I have a decent amount of money in the account and plan to buy and hold with this money.My question, over the long haul what is the best option?  

He and a partner are in it for the long (20 year) haul, but they have ended up with none of their own money into it.  

My oldest daughter will be at kindergarten age around the time we would be moving.Do you plan on repeating the process or are you going to stay put for the long haul?

But the city has risks too: historic tanneries, dry cleaners, gas stations, garages, workshops, any kind of industrial use - always be suspicious of what people did with chemicals back in the 50s and 60s when the general population had no awareness of the damage I just had to turn down a small development  10  house's or 20 detached as phase 2 found chemicals for the Filbert orchard ( Filberts are hazelnuts ) that was planted 30 years ago.the soil had to be dug down 1 to 2 feet analyzed and hauled to special dump at 3X normal dump fee's.. there is a reason why we do phase 1 and phase 2 and just dont buy this dirt and take on those liabilities.. now to be fair this is for lending purposes is someone want to buy it the county / city would not require the phase 1 or 2 but you take on going risk of someone suing the pants off of you in the future.

Been a long haul.

On the other hand, if the house is not entry level, the buyer is a wealthy, he will not need a loan and an expansion might make it more desirable.One additional point which you alluded to.

We also did that previously in a house built in 1840 obviously with no insulation.We're in for the long haul and want energy usage to be as low as we can.

Everyone who owns an older home has dragged all the soggy belongings (furniture, appliances, clothes, toys, knickknacks, etc.) out to the streets which are covered in mud, and there are downed trees, fences, pool cages, boats on front lawns, a major mess.