Also-vinyl/shingle with three bed rooms are the best. 

(I'm house hacking and don't plan on staying there for more than 2 years, so I wouldn't get too comfortable with my garage space), plus the extra income is more appealing to me anyway :)  So my questions are:-will fixing the garage structure and getting the roof done (re-shingled) have a decent positive affect on the property value? 

We have a particular type of shingle (T-lock) that most insurance companies will not cover but that's because of the high failure rate, not because of age.I also don't understand why they wouldn't cover an out-of-state investor.

I went and seen it today. 1/4 of the rear fascia is gone, some of the soffit has vegetation growing on it, the shingles looks “okay”, the wood under the shingles are planks, the crawl space in the attic is very small, the air handler will more than likely need to be replaced, because of mold concerns I would budget for the duct work as well, but I would wait for the a/c guy to look at it.

But if you would like to put you're shingle out a bit further, you can join these two groups and will have plenty of requests: Private Money Billboards, and Real Estate Wholesale deals.  

That's why I'm trying to be conservative.The $22K is roughly as follows:$5K - new shingles (this is a quote from a contractor)$5K - conversion cost to separate utilities + new water heaters (will definitely either separate the utilities or buy efficient, tankless water heaters)$4K - plumbing$2.5K - new carpet and paint (needs carpet in 1 unit only)$2.5K - 4 new tubs, toilets, sinks$1.5K - sheetrock$1K - landscaping$500 - new fixtures, misc.Some of these costs are low because all of the work is being done by my father in law and/or his friends, who give us great deals on labor.

We can't throw away over $500 on an application fee, and a wing and a prayer that FHA inspectors wont come through and tack thousands of dollars on our budget to remove this paint, replace that shingle, and patch this hole.

Post a floor plan, that will help.Nicest conversion I have seen with an old retail space got rid of the show windows and replace with bow framing with double hung on each side of a picture window with shingles over the top on the built out wall.

You might get lucky and pull it off, but only after you had to throw the first few batches in the trash until you got all the steps in the right order.So if we tell you...House, paint, 2x4s, mortgage, shingles, 5/4 deck boards, toilet, real estate agent, taxes, title insurance, llc, income tax, 1031, $1250 mo rent, backup exit strategies.Can you flip a house?

The roof looked good to me visually, but what I didn't realize is that there was 3+ layers of shingles up there.