I was also interested in Burlington City based on analysis (CoCROI, 2% Rule, 50% Rule etc....) and the revitalization efforts, which I guess is all speculative.  

Flipping is really speculation subsidized by a deeply discounted purchase or creative financing justified by the sale, with renting as the most likely plan B to break even monthly at the least. 

I'm speculating that the houses will hold their value and mortgage paydown will be my profit down the road, but I'm sure people in Detroit thought the same thing.There are hidden expenses that you don't see.

Attorney is placing a Phase 1 ESA approval contingency into our offer.Let’s speculate for a moment that the property passes either Phase 1 or Phase 2 ESA and we purchase. 15-20 years down the road we're ready to sell. 

I think everybody is speculating on the next big gentrification area. 

Are you speculating and investing for appreciation...or looking for stability...what types of assets are you after...and you're leveraging bank money...$50k isn't going to get you very far...you're going to land on a Midwest metro area with limited funds...and the only right answer is what you are most comfortable with...all the major Midwest cities are going to have some similar characteristics...and all of them will have deals. 

But it all depends on how rigorous you are in estimating your expenses (and I suggest to err on the side of being more rigorous, than "flexible") and your investing criteria (maybe you are ok with large down payments, or with getting only 5% C/C ROI, or barely breaking even on cash flow since you are counting on appreciation/speculation).

If you are looking for speculative appreciation, the larger cities are good possible investments, however, the prices have already risen significantly so it is very hard to find good deals.Smaller towns and cities that haven't yet returned to their 2008 prices are where I recommend people to invest.

Buying in an up and coming area in hopes that prices will go up is speculation. 

I have heard people say on your first deal you should invest in your backyard, but I don't want to invest for appreciation (I find it a bit speculative, especially right now with rising interest rates).