I am also in the Massachusetts National Guard, my 10th year anniversary was January 2018. 

Build some kind of a mesh guard, maybe out of chicken wire, so debis cannot clog the drain.  

It really got me fired up and let me tell you, if I didn’t also love my home in guard-gated community and lifestyle with my 2 & 4 year old I would be house hacking and living off half my income.

Naturally, I am extremely on guard now and don't want to take the seller on their word at face value.

From the IRS website https://www.irs.gov/taxtopics/tc511"If you're a member of the National Guard or military reserve, you may be able to claim a deduction for unreimbursed travel expenses paid in connection with the performance of services as a reservist that reduces your adjusted gross income rather than an itemized deduction on Form 1040, Schedule A.

@Travis Rasmussen a lot of folks on BP use REI Guard, although I think they go by a slightly different name now.

@Benny Gelbendorf The roof and gutters would be around $1000 (fix top few rows of brick on chimney, replace pipe boots, split boot on electric meter mast, new gutters & downs, maybe gutter guards on some areas)The mold I do not know, I would imagine in the $1000 range, but would need an inspection from a mold expert.I am an exterior contractor and my partner is a handyman/general contractor.

The fact that the old guard seems to be doing just fine (albeit with a bit more effort) suggests that this is probably newbie error :)

As though the seller is lulling me to drop my guard.

Guthrie now lives in a rental a few blocks away.It’s in a safe neighborhood where private security guards patrol at night.