Though this Divorce is official, my focus is to make sure that my struggle and pain isn't transfered to them, but that my legacy is set in place for them.

Landlords will owe tenants three times the deposit amount, plus 5% interest, plus attorney’s fees, plus other court costs, unless they do all of the following: Put the security deposit into a bank account The bank must be in MassachusettsThe account must earn interestThe account must be under the tenant’s name and social security number only, with landlord as signatory (specifically, a landlord-tenant account)Note: credit unions are not banks (we are looking for the case, but it was Western Housing Court circa 2001)Within 30 days of signing the rental agreement, give a receipt that lists The name and location of the bankThe amount of the depositThe account numberEach year, Pay interest Either 5% or the actual amount of interest received (if less than 5%)Either cash or check or deducted from the rentGive an annual statement that lists basically all the same information again The name and location of the bankThe amount of the depositThe account numberPlus the interest earnedWithin 30 days of the end of tenancy, Pay all interestProvide an itemized list of damages This list must be signed by the landlordThe form must say “Signed under the pains and penalties of perjury”Receipts, invoices, or photographic evidence are required for each deductionNo deduction can be made for damaged items identified at move-inReturn the original deposit plus remaining unpaid interest less damagesAny single failure of any bullet point or part of a bullet point above will entitle the tenant to receive three times the amount of the deposit.

If it is so old and rundown that it causes a health or safety hazard, you would have an argument, but if it just looks outdated you likely have no leg to stand on, legally, since you rent a property in as-is condition.

I am hoping the issue is corrected, but it pains my heart to know I spent that kind of money on ONE TOILET repair.I do understand that it pays to learn in any business.

@Thomas Paine I think it really depends on the market...

Determining existing conditions and the scope and cost of renovating them and other project scoping requires time, money, patience, as sense humor and maybe even an attraction to pain :). 

She was also a pain on her move out and stayed 10 days past her move out date, because her loan fell through on her other house putting me in an awkward place with the next tenants.

At the time, it was a pain in...

With real estate, you maintain much more decisionmaking control and although we experienced a wicked housing collapse last decade, many real estate investors can still argue they maintained cashflow and that their respective market didn't feel the same pain others did.The knocks I would have against real estate is it is significantly less liquid and the fees are much higher when it comes to buying, selling and financing.With the introduction of Robin Hood, it's a race to the bottom as brokerages have been slashing trading fees in recent years.In my mind, there is nothing more passive than buy and hold stock ownership, though you may be relying more on capital appreciation, whereas many real estate investors prefer passive cashflow.

Depends on the deductions.I had several MF's and some years back before ObamaCare, when I quit my corporate job, I bought my own health insurance , about $1,500/month which I couldn't deduct.