My best was 3 months for a 1800 SF colonial gettinf walls knocked out, kitchen, baths, roof, windows, siding, driveway, boiler, electrical service, not quite a full gut, but close.

Both rental properties had a claim filed against them and received payout.Property 1: Claim for $21,000 was paid out to fix/replace roof, guttering and siding.

Needs a new roof, possible foundation issues, and each unit needs some TLC, which is why I want a lease option in case I find the foundation is too much to handle or something.

I have been looking at 2-4 unit multifamily properties (3b/1.5b) in the Southington, CT area I did a site visit with my handyman.Property is in good shape new roof and deck, except for aluminum wiring and cosmetic items.This market has been very competitive the last year and decent properties don't stay on the market too long. 

Do you have reserves to handle replacing a $3,000 furnace or $7,000 roof?

I have not walked the property, only drove by the location so I can not speak to some of those vital questions that you inquired, but the location is really good, and the structure from the street seems solid, with a newer looking roof on one of the units. 

My inspector failed to properly inspect my roof and consequently leaked 2 weeks after I closed.

What's the condition of the roof, boiler, chiller, etc? 

Separately, I've noticed that you could build (nearly) turn-key log cabin home kits to put on these plots of lands in the 1000-1250 sq ft range for  ~100K (I say nearly as I'd be doing the roofing, some electrical/some plumbing/minor details-- I have experience with these).

And everything will be completely new afterward because I'm doing a 95% renovation (only the ext walls and roof are not being touched) as a result of a fire.Thanks in advance for your feedback.