2) I've been told that it's all what you and your family's tolerance levels are.  5 people in a 2br/1ba will definitely be quite tight.  

Yes, the market is tight, but there are still some needles in the haystack.  

If you're really getting it for a steal, say 50-60K under market value in present condition, then you have room to give up some of the deal in exchange for a loan for the downpayment and/or repairs.But if you're only getting it for 10 or 20K under market, it might be too tight for a lender to take a chance on a riskier 2nd position mortgage especially if it needs rehab.

I think those numbers are too tight.

Many will likely respond that, with a nice home in a nice area with high demand, you should self-manage.There does not seem to be much that you can do in this situation aside from sitting down and setting expectations, managing the manager tightly (I know, this defeats the purpose) and, long-term, shopping for the best manager.  

I have until Nov. 7th so tight deadline.

I find these to be more practical for flippers or people with a tight financial profile.

The numbers DO seem tight, but if you have connections where you can save some money such as closing costs etc. then it may be worth it.

Of course the finish out choices and the area that your property is in may affect how quickly it sells and at what price but as long as your documentation is tight you should be good. 

I'm mostly looking for a starter home to be able to pay off quickly and become more financially independent and as a result I'm on a pretty tight budget of 50K-100K.