Should I make an offer before it's gone?!

[Brandyn Dietman]

Hey y'all! I found a property that I like (I'll be owner occupying), however, it will need some work (plumbing, hvac, possible roof) however I think the price could be right. The only down side is I will have to put the money into it, and if I want to move into another investment property in the next 2 years, will I have the money to do it after investing in this property. Conversely, I found another property, more in the area I want to be, but the owner wants too much for it (about $35,000 too high) and has indicated this is his retirement money property so he doesn't think he'll take much less.. I know the unit I like, has had 3 showings in the last 3 days and I don't want to lose it. The other property we like but is a little high, we have a showing set up for Wednesday. My question.. Should I try and place an offer on the property that needs some work to try and get an accepted offer to have it under contract so I don't lose it? And then see if the higher price property is more for us? What have y'all done in this type of situation? Thank you!!! Milwaukee, Wisconsin