are there recommended contingencies to place in the contract , as it relates to wholesaling?

With more units, bigger budgets, making it easier for the HOA to absorb (not always tho)2) having someone on the inside is key, they can share with you information as to the true health of the HOA and politics. 3) FINANCIALS - Need to see balance sheet and P&L.

If they have been paying their rent, and there aren't any expenses related to poor upkeep of the home on the tenants part, then I wouldn't be too worried.  

My partner and I are relatively low volume (3-4 projects per year).

@Felix L PerezThere is a lot to explain, so probably you should get with a tax accountant.The short answer is: expenses specifically related to this property (purchase, rehab, holding costs etc.) should be shelved until next year and deducted against the sale price.

Now from some of the things i read that could be because they do not want to deal with HOA related costs that could be past due, even if its 1k.

Also for rehabs, what software do you use to track expenses related to type of work completed (electrical, plumbing, etc), and what features have been important to you in your business to analyze historical expenses on rehabs?

I know there has to be no connection from the IRA to the investment (relatives). 

On a related note, I was planning on traditional lending with a 20% down payment.

You want to investigate any building restrictions the municipality may have related to zoning, setbacks, lot coverage etc.