financing my first rental property - two questions

[Joseph B.]

Hello bigger pockets! I can't believe it's my first post here; I've been reading in the forums and listening to the podcasts for the past year trying to get educated on real estate. I've had a really good paying job for the past 2 years and at this point I'm looking to just pull the trigger and buy a house to get my feet wet. My long term goal is to retire through real estate. 2 Questions:

1) If you were to choose between buying a $300K house and a $150K house as your first rental property ever, which one would you choose (all else being equal)? In both cases I can get 3000$ or 1500$ in rent per month respectively. I'm pretty sure I can get qualified for a 300K loan. Ideally, I would rather buy two $150K homes for diversification purposes but this question is something I've been wondering about: if I choose the $150K option then the bank might not let me finance another $150K house for at least a year...  which might set me back. Is that true or false? Isn't it better to use my "first property joker card" in a larger house? 

2) My brother is in a similar situation as me - good paying job and ready to buy his first rental property. Is it better to buy properties as a 50/50% owner with him or should we just do this separately? I know this is a broad question but I am trying to view this from the perspective of getting financing for multiple properties.

Thank you so much for your help and I look forward to continuing this conversation!