Resist the urge of going overboard on his return because you want to do this over and over again, so it has to be sustainable for you both.

I've come across the same resistance from agents who want me to use their own private financing connections and I get the idea most agents aren't qualified to write such a contract especially if there are any unusual considerations.My question to you is- Do you feel it is a good idea for both parties to use the same lawyer to write the contract and follow the deal through?

Barrier of entry is always high in the Peninsula, but once you get on the train, it is pretty much automatic and crash resistance.  

If you do, don't put carpet in the basement until you are absolutely sure it's dry after heavy rains and use mold resistant dry

If this is purely an investment property (and it sounds like it is), that could be part of the reason for the higher interest rate and level of resistance you're seeing.

I used conventional financing (I believe the loan was sold to Fannie Mae) with a 25% down payment.This is the first and only property that I own.I am currently looking at purchasing a personal residence (I currently rent), however I have been been met with resistance trying to obtain a loan.My credit profile is excellent, I am looking to put approximately 20% down and I do not need the income from the investment property to qualify (although so far it looks like rent will not be considered so in effect it counts against me).Does anyone have thoughts on how to obtain another loan?

If you don't have money or credit, I would suggest becoming an ally with someone who does.Overcome resistance with persistance.

When you go to increase every year you will typically get less resistance as you are the best or one of the best deals in town.

Persistence breaks resistance. 

It is said that a successful person can lose it all and get it right back much quicker because they have learned from their successes and failures and can now take the least path of resistance.