These are mostly older, 100yr old homes with all kinds of styles and sizes. 

Ok Thanks to both of you for your kind replies.

Don't shoot for those kinds of returns here. 

I wasn't sure what to say at that moment LOL what would be the best way to answer that kind of questions? 

Seems like two kind of people out there....one's that focuses on keeping a tight hold of their assets and one that ignores their assets they've built while going out to obtain new assets

It's a pretty tight market so I'd be curious to hear what kind of strategy you're looking to deploy. 

Unless that deal is a pocket listing or other kind of off-market deal, the property has been exposed to the market so its current value is exactly what you are paying for it, not a penny more.  

I would only lend that kind of money if it was secured against something, such as the property itself. 

We plan to begin our investing in Cleveland, but are open to exploring elsewhere.About 6 months ago, my father, brother and I were having breakfast and I started kicking around the idea of splitting a vacation home. 

She goes into the kinds of work you should (reasonably) do yourself vs. the things you should contract out.