The older the house the higher the insurance.

Further, I've heard it takes upwards of a year to season a rental rehab: are there any tips anyone has to shorten this time?

Sometimes they are located in some older areas of the city and may need a ton of work.However, if you live in a costly market, then it is probably wise to go with another market.

When trying to obtain financing for an investment property , how do you get around not having seasoned funds in your account.

I am curious how seasoned investors use craigslist?

*Buy an older multi family unit/s, rehab and either flip or re-lease at higher rents.

And, the right questions are formulated as you become seasoned in your experience and understanding your risk level.  

Try and find a new tenant before you hit the dead season, and move on.

Essentially a fix and hold strategy.However, even if the property doesn't need any fixing, you can use hard money as a bridge loan, season it for 6 months, and then refinance into a conventional loan. 

The renter has three children older than 6.