Wondering how much analysis and research is sufficient to make an offer and what details/assessments are better saved for the due diligence stage?

I've been looking in Naperville for over 6 months for both Condo's and SFH's, and the taxes, Condo Assessments and HOA's all drive the cost up where it's pretty difficult to get a cash flow of over $100/month without putting do a very large downpayment. 

I figure they need to know to assess risk and stay in business.

Once I found it though I moved quickly to assess and submit a deal with my realtor.

Return on investment will be significantly higher with a lower down payment but you may have trouble finding homes that cashflow with a lower amortization, etc.Would be happy to chat further & do a deeper assessment.

Also it’s important to evaluate the general health of the homeowners association to ensure they have proper reserves for capital expenditures etc and you won’t be hit with special assessments. 

Is there any major deferred maintenance that they're going to nail you for an assessment?

@Tony Marcelle  The probate records are still free, but it will require you to visit the Jefferson County probate court rather than assess them online.

@Amber KennonYou and your father should first consult with an agent who can give you a fair assessment of the value of the property.A lot of people may be reaching out to your father with offers but you won't know if they are good offers without knowing the true value.Seller financing is one option for your dad - He can sell the property and instead of dealing with tenant issues(which it seems like he does) he can instead collect a payment on a monthly basis from the ultimate buyer.He can negotiate an interest rate with the buyer which can help him into his retirement.The other alternative is that he continues to live there and you inherit the property from him.

So if we now have a loan house #1 and a paid off rental now on house #2, how can we get qualified to get another cash out refi for house #3 out of the re-assessed equity from #2 when we no longer have the DTI to qualify for #3 (due to the new debt from house 2 )??????